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Find Places to Stay in Chestertown on Airbnb

Find Places to Stay in Chestertown on Airbnb

Discover entire homes and private rooms perfect for any trip.

Places to stay in Chestertown

Places to stay in Chestertown
A spacious private apartment right in the heart of beautiful downtown Chestertown! With food, drinks, and shopping literally steps from your front door, it doesn't get better than this. The Bittersweet Apartment is a subsidy of The White Swan Tavern.
  • The place is close by to everything I'd need, but also quiet. It was also very clean and well-stocked.

    Esther2020-03-09T00:00:00Z
  • Such friendly service and kind hospitality from hosts. The location is wonderful and convenient.

    Kelsey2020-02-23T00:00:00Z
  • Just a great, very clean apartment right in the middle of town so everything is within walking distance. A very quiet retreat and especially loved the living room with all of the windows over looking High Street. We spent an entire afternoon in that room just enjoying and relaxing. Great hosts.

    Mike2019-12-16T00:00:00Z
  • The apartment was very comfortable, clean and well located. Large comfortable bed, large bathroom, well equipped kitchen. It is located on the second floor, steps from everything in the town. I highly recommend it!

    Marian2019-12-13T00:00:00Z
  • Cute spacious 1 bedroom apartment right in the heart of downtown Chestertown. Communication with Sarah was great. We loved the place. You can pretty much walk to everything from this location. There is a large living room, full kitchen and nice sized bedroom with a king bed and 1 bathroom. It was perfect for us and we would definitely stay here again!

    Korene2019-11-18T00:00:00Z
  • Perfect location for Chestertown events, we parked the car and had no need to move it. There is a fairly steep set of steps: 10 steps, a small landing and 10 more but well worth the climb for the location. Chestertown is one of the nicest towns we've had the pleasure of visiting.

    Beth Ann2019-11-03T00:00:00Z
  • Spacious and clean one bedroom apartment in downtown Chestertown. We very much enjoyed our stay.

    Stephen2019-10-27T00:00:00Z
  • Sarah’s place was amazing! She’s an amazing host. Would stay here again.

    Trisha2019-10-13T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Flat


    Accommodates

    4


    Bedrooms

    1

    Chestertown, MD, United States

    Charming 1880's home in Chestertown's Historic District. My home is comfy, cozy, & convenient to the center of Chestertown & the river. Fully renovated with all modern amenities. While here, guests are walking distance to shops, coffee houses, and restaurants in our lovely town and a short drive to Washington College.
    The house is both cozy and spacious. The living room flows into the dining room with a modern kitchen at the back. Off the kitchen is a large screened porch with overhead fan for warm days. The 2nd level has a bedroom with a full bath just across the hall. A walk in shower and double sinks give guests plenty of space. Laundry is also on this level. Steep stairs lead guests to the 3rd level - a truly private retreat - with bedroom and full bath. A small area off this bedroom has a single-sized daybed for an extra guest or used as a serene reading nook. The backyard is fenced. There are 2 cats & a dog that live here. If you have pet allergies, this might not be the right fit for you.
    Chestertown is an idyllic place - a town steeped in history. It has gorgeous architecture, quaint charm, a vibrant and ever-growing arts scene, and the River.
  • We really enjoyed staying in Franna’s comfortable and charming home. It is an old home with nooks and crannies, built in cupboards and closets and wonderful wooden floors. In addition to two porches, a small living room, dining room and well arranged kitchen, the house has two bed rooms and 2 1/2 baths over three floors and is well suited to accommodate two people or two couples. As mentioned in other reviews the steps up to the third floor are steep and therefore not suitable for everyone to climb. The house is ideally situated in Chestertown, within a short walk’s distance to the stores and very good bakery. Communicating with Franna was easy with quick responses. I would definitely recommend staying here.

    Mary-Lou2020-03-14T00:00:00Z
  • We loved our stay at Franna’s place! Perfect for a little weekend getaway. Great location, can easily walk into town in 5 minutes or the river in 10. Fully equipped kitchen, so we were able to cook dinner no problem! Plenty of towels and blankets. Comfortable beds! Highly recommend Franna’s place if you’re coming to Chestertown!! Would stay here again. Also- We had dinner at “The Kitchen at the Imperial”.... sooo good!

    Callie2020-02-17T00:00:00Z
  • The stairs are step and bedrooms are on upper two levels. I now understand why it isn’t for kids. It was also a challenge for my mother who is her 80’s so she crashed on the couch. Otherwise, everything is great.

    Karen2020-01-26T00:00:00Z
  • This historic home is perfectly nestled in heart of Chestertown. There was plenty of space for sleeping and a perfect kitchen (not they we needed it). The hosts were extremely accommodating. Thank you.

    Carolyn2019-12-01T00:00:00Z
  • This home is stylish, comfortable and extremely convenient to local restaurants. This is one of our favorite places to stay in Chestertown. Hosts are awesome!!

    Lisa2019-11-23T00:00:00Z
  • Perfect location when visiting Washington College. Comfortable, clean & welcoming home with all necessary amenities. Great communication from our host. Everything went smoothly. Easy parking on the street.

    Karin2019-10-27T00:00:00Z
  • We enjoyed our stay in this clean, comfortable, historic house!

    Jane2019-10-03T00:00:00Z
  • Franna is an accommodating host. Her place was charming and great location in town.

    Christine2019-09-29T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    5


    Bedrooms

    2

    Chestertown, MD, United States

    Waterfront property on a peaceful creek. Ideally located in quiet neighborhood, 10-minute walk to Washington College and historic Chestertown. Private floor with two bedrooms, full private bath with beautiful large shower. Kitchenette has microwave, mini fridge, and coffee maker. $20 fee for each additional person over 2. Free parking. WIFI. Shared entrance with me but privacy assured. Hiking/biking, farmer's market, cute shops and restaurants easy walking distance. No cleaning fee or deposit.
    I'll be here with my friendly dog, Nacho, to greet you and give advice about anything Chestertown-related, but I also want you to have your space and your private time. The upstairs is all yours and you will only share it with those with whom you are traveling. I'll provide coffee/tea, but will give directions to Chestertown's fabulous breakfast haunts for more goodies. Nacho is very happy to greet guests, including children, but no other dogs, please. Not ADA accessible and requires that one climb stairs to access upstairs rooms from the entryway.
    You'll want to try the famous Evergrain Bakery for breakfast, or Play It Again Sam's, or Figg's Ordinary ( gluten-free). Boat rides are available on the beautiful Chester River, and almost any weekend will bring theater, art gallery exhibitions, festivals, etc. here to town. A short walk will take you to many restaurants and shops. Don't miss the new Casa Carmen Tapa Bar in town!
  • This Airbnb was very clean and tidy and had everything I needed. Easy access to wifi and easy walking distance to downtown!

    Brady2020-03-07T00:00:00Z
  • Hi Jan. Mike and I had a wonderful stay at your lovely Airbnb. You were so kind and thoughtful to all the special details. Everything was fresh and clean and we loved the tea/coffee and biscuit station. You were great at keeping in touch and remaining flexible to our arrival time. Nacho is a sweet and friendly greeter waiting at the door with his tail wagging. My only regret is not being able to stay longer! Thank you so much for opening up your charming house to us! Cheers... Anne and Mike Province

    Anne2020-02-29T00:00:00Z
  • Rooms were great. Clean and cozy. Jan and Nacho were nice enough to wait up for us as we arrived late due to weather. Will likely stay again if we come back to the area.

    Greg2020-02-28T00:00:00Z
  • Lovely space on a quiet street. Jan met us and made sure we had everything we needed. Fluffy towels and comfy bed. Would recommend!

    Katy2020-02-23T00:00:00Z
  • This was my first stay through Air BnB and I was thoroughly impressed. Jan was communicative, warm, and hospitable. The place was in incredibly clean and the bed was beyond comfortable. Cozy, comfy, kind—all you need.

    Doug2020-01-26T00:00:00Z
  • Jan and her little dog, Nacho, are delightful and welcoming. The space is amazingly clean and nicely laid out with a comfy sofa to lounge on, a very comfortable bed with lots of warm coverings (I stayed in January), a really nice bathroom, and microwave/fridge/coffee maker that is great for reheating leftovers or snacks. The space is private and spacious. I plan to come back on future visits to Chestertown.

    Hilary2020-01-20T00:00:00Z
  • Jan's place was amazing! The beds were super comfortable and both rooms were spacious. The bathroom was clean and the shower was very nice. It was a quiet house and we got great rest. I will definitely book again!

    Jody2020-01-15T00:00:00Z
  • My husband, baby, and I stayed at Jan’s for a night and really appreciated the ease of communication and cleanliness of the place. We made last minute reservations for a funeral and it was ideal. I know chestertown pretty well having gone to college there, and Jan’s place is the best of it!

    Jeanette2020-01-12T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Flat


    Accommodates

    4


    Bedrooms

    2

    Chestertown, MD, United States

    Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking, fishing. Pets welcome. We donate 5% of Airbnb proceeds to Save the Children, the Kent County Humane Society, or ShoreRivers conservation—your choice. Make it your home away from home for a weekend or a longer stay.
    A ground-floor guest suite adjoins the main house but offers total privacy with a separate driveway and entrance. Hardwood floors, comfortable furnishings, WiFi, Smart TV with access to Netflix and Amazon Prime, separate controls for heating and air conditioning from an eco-friendly geothermal system. Enjoy lovely water views from the living room, a cozy bedroom with queen bed, dresser, and ample closet space, and a fully equipped eat-in kitchen with complimentary coffee and tea. The living room has a sleep sofa to accommodate up to two children or guests (please contact us for particulars). Bird watchers will enjoy many species, including ducks, geese, osprey, bald eagles, great blue herons, and owls.
    It is a small, quiet and very friendly residential neighborhood. There is a small park with playground equipment, dock, and sandy beach a 3-minute walk away. Bring your bicycles, scooters, running shoes.
  • Extremely convenient to town, great walking for dogs, and very private space with separate entrance and lovely view of the river. Highly recommend.

    Lisa2020-03-09T00:00:00Z
  • This is a lovely guest suite. It was comfortable, relaxing, clean, and the bed is super comfy. It was mentally therapeutic to sit outside on the dock and take in the fresh air and the sound of all the geese. Highly recommended!

    Linda2020-02-28T00:00:00Z
  • Clean and as-described. Thoughtful touches all around with the best welcome guide book you'll ever read. Great, close views right on the Chester River. Great space for dogs w/of an absurd upcharge. Extremely quaint town, with a charming and content small-town vibe. Checking out Sado Sushi and Bookplate Bookstore are must-dos! Stay here for a comfortable and relaxed hideaway for a weekend recharge or to explore the Eastern Shore

    Teryl2020-02-09T00:00:00Z
  • Tom's place was wonderful. The view overlooking the water was fantastic with lots of geese and eagles flying by. It was winter so we didn't kayak but it would be a great place to kayak. Check in couldn't have been easier and when I needed some assistance getting the Superbowl on the TV, Tom responded promptly and helpfully. There were lots of nice touches such as some home baked goodies and chocolates. I highly recommend it.

    Elizabeth2020-02-04T00:00:00Z
  • A beautiful spot to relax and a great little historic and dog- friendly town! Perfect for a weekend get away.

    Sherry2020-01-20T00:00:00Z
  • A lovely, tastefully decorated bungalow. The property is well cared for and sparking clean. We were there in the winter but the water front location looks like super fun during the warmer months. I would recommend this Airbnb readily

    Bronwyn2019-12-26T00:00:00Z
  • This place was great!

    James2019-12-11T00:00:00Z
  • Wonderful stay on the water, Tom and Jen were so quick to respond and even left a little note with treats for my dog. They have a manual with tons of info on the area that we found incredibly helpful. Most relaxing weekend I’ve had in a long time.

    Kim2019-11-12T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Guest suite


    Accommodates

    2


    Bedrooms

    1

    Chestertown, MD, United States

    Two blocks from Washington College, downtown Chestertown and 4 blocks from the water. Quiet, private while still in town.
    Walking distance to college, shops, restaurants, groceries, coffee shop, water and parks. There are rails to trails for walking and running.
    Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    8


    Bedrooms

    3

    Chestertown, MD, United States

    Delightful carriage house, newly painted and furnished, at the rear of a Victorian row house . Covered parking, within easy walking distance of downtown Chestertown
    Upstairs, overlooking an enclosed garden, with an all-new tiled bathroom and fully equipped kitchen. Wooden floors, rugs, built in cupboards and all necessary linens, towels, and paper goods.
    Chestertown is one of the most complete and beautiful historic towns in the Mid-Atlantic region, with unique stores and restaurants all within easy walking distance. Shortly before your stay we will send you comprehensive notes on the house and town.
  • Comfortable, with beautiful lighting fixtures!

    Emily2020-02-20T00:00:00Z
  • A charming space with modern touches that's a short walk from all that Chestertown has to offer. We highly recommend it.

    Kevin2019-12-08T00:00:00Z
  • Roland's place is perfectly situated in Chestertown. An easy walk to High Street and Washington College, we were home from dinner in no time at all. The space is well appointed and well thought out, would stay here again on a future trip to Chestertown.

    Ethan2019-11-16T00:00:00Z
  • THE perfect place to stay when in Chestertown! We attended the Sultana Downrigging Festival and we were able to walk everywhere we needed to go. It was great to be able to park in the garage! The efficiency apartment was perfect for the two of us and, although we didn't cook, there was plenty of room and equipment in the kitchen to make meals. There were lots of washcloths and towels in the bathroom and everything was amazingly clean. If we ever go back to Chestertown (and I hope we do), we will definitely stay here again.

    Bettina2019-11-04T00:00:00Z
  • A charming "garret," with high ceiling and beams, stylishly designed in crisp whites, blacks, natural wood, dull blues, and a touch of yellow in the kitchen.

    Susan2019-10-27T00:00:00Z
  • Wonderful stay

    Laura2019-10-18T00:00:00Z
  • The place was great and everything we wanted was within easy walking distance. We had a lovely time and I expect we will come back.

    Stephen2019-10-14T00:00:00Z
  • I love this spot. this is my third time staying here on a work trip. the space is perfect for those who don't want to be confined to a hotel room and want the independence of cooking your own meals.

    Karrah2019-09-10T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Guest house


    Accommodates

    2


    Bedrooms

    0

    Chestertown, MD, United States

    Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.
    We do have a pull out queen sofa bed in the living room for 2 additional adults or children and a smaller couch in the loft that is fine for a shorter adult or 2 children in sleeping bags. We have 3 kayaks, 2 inner tubes, dock for boat, loft with coloring books, tent provides getaway spot in any weather! Wood stove working for fall/winter, outside fire pit all set up with firewood and chairs. Small barbecue grill & charcoal. You can even come by boat, we have our own dock. Amazing bird watching!
    Very safe neighborhood for walking. Easy 1 mile walk into town, a wonderful town! Saturday Farmer's Market is fantastic! Reflective leash in closet for walking your dog at night.
  • Everything about PJ’s cabin was perfect for us. It is convenient to downtown Chestertown yet feels like you’re in a secluded paradise. PJ has thought of and included every comforts of home in the cabin — they even had a fire built for our arrival. It was truly a little slice of heaven! We will definitely be back.

    Abby2020-01-05T00:00:00Z
  • Pj’s place is the perfect quiet getaway. We loved sipping coffee on the dock. The house is very clean and stocked well. Pj made check in a breeze. It was a relaxing trip away from the hustle and bustle and we enjoyed it very much.

    Samantha2020-01-01T00:00:00Z
  • What a FANTASTIC place--perfect for our girls weekend getaway on the waterfront of the Chester River. PJ was the perfect host: quick to confirm, welcoming, and helpful with both ensuring that we were clear on all of the amenities of the house and had recommendations for getting out and about in nearby Chestertown. Warm, super cozy home in the fall/winter (with indoor fireplace and outdoor fire pit) and dog-friendly. BEAUTIFUL sunsets and secluded feel. We can't WAIT to come back in the spring/summer to make use of the kayaks, inner tubes, and fishing poles. Thanks, PJ!

    Holly2019-11-17T00:00:00Z
  • PJ’s place is like a home-away-from-home. It is quaint and cozy with everything you could possibly need. It’s a wonderful place to enjoy the tranquility of the water and nature. Also, a walk into town is totally do-able! We love it here and are already looking forward to coming back!

    Cassidy2019-11-10T00:00:00Z
  • The house is just the right setting for a restful weekend near Chestertown. A short walk to town.

    Don2019-11-04T00:00:00Z
  • Very nice cottage in Chestertown! PJ was more than helpful! We look forward to our next trip!

    Jose2019-10-27T00:00:00Z
  • We had a wonderful stay. Pj made the whole experience seamless. House was just perfect for visiting our son at Washington College for Parents' Weekend. Location was amazing for all Chestertown has to offer. Had the opportunity to spend much time out on the dock and in the kayaks. Will definitely be coming back!

    John2019-09-22T00:00:00Z
  • Loved staying at Pj's very clean and homey. Too many amenities to mention, Pj has thought of everything you could possibly need, especially if you forgot to bring something and that makes staying there extra special. We brought our boat and it was so nice to be able to use the private dock there. Very close to town but very quiet and peaceful. I highly recommend. Definitely the best place to stay!!

    Joan2019-09-18T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Cabin


    Accommodates

    6


    Bedrooms

    2

    Chestertown, MD, United States

    Charming Bungalow with great indoor-outdoor entertaining space. Fully renovated, 2 bedroom, 1-1/2 bath. Sitting Room, TV Room, updated Kitchen, Screened in Back Porch, pet friendly, fenced back yard and doggy door. Located in the Historic district on the Main Street; walking distance to Washington College, restaurants, coffee shops, book store, retail shops, Saturday's Farmer's Market and Chester River waterfront. The perfect location for exploring Chestertown, Kent County or the Eastern Shore.
    A newly renovated home with spacious rooms, a fully modern kitchen, fenced in back yard and a screened in back porch with seating area. The back door of the house has a doggy door for easy access to the back yard for your dog.
  • Great home in cute town. Would stay again.

    Derrick2019-07-28T00:00:00Z
  • We had a great time staying at Jon's place. It is an adorable cottage with enough space for a family and if you have kids they've got puzzles, games, and books on the book shelves... so your kids can't complain "I'm bored." We enjoyed sitting on both the front porch in the evening and the enclosed patio out back for coffee in the morning. The house is clean and nicely decorated... kitchen is all set up for cooking and a BBq out back. We had things to do all weekend. Wish we could have hung out more in the house. We would stay again in a heartbeat.

    Melanie2019-07-14T00:00:00Z
  • We had a wonderful time at the bungalow! It is walking distance to all that Chesterton has to offer, which makes for an enjoyable weekend. They made the trip smooth from check in to check out. The space was better than it photographed with thoughtful touches all around. Bonus of a great backyard if you bring your pup. Highly recommend I am sure we will be back!

    Robert2019-06-16T00:00:00Z
  • This is our second stay at Allie's Bungalow. The location is great, in town and walking distance to everything! Nice bedrooms, kitchen, bath and back yard. The internet service was fast and stable. Our dog really enjoyed the doggy door to the back yard... self serving for the first morning walk! Our week stay involved steamed crabs, National Music Festival events, wine tasting, dog park runs, golf, biking, farmers market, shopping, a sunset dinner cruise and hikes in the Eastern Neck National Wildlife Refuge! Chestertown is is filled with great fun and Allie's Bungalow is the place to stay!!

    Peter2019-06-15T00:00:00Z
  • Great location and convenient to everything! Such a cute little home and I’d definitely recommend it. We fit 4 of us very comfortably. Loved watching thunderstorms this weekend from the screened in porch!

    Jaclyn2019-05-27T00:00:00Z
  • My friends and I came right before Tea Party Weekend and had an amazing stay! The backyard was perfect for my dog and we were right on the parade route! Jon, Barb and their daughter were really great hosts, and incredibly responsive when we had trouble with the cable and internet. I would absolutely stay again the next time I stay in Chestertown!

    Lael2019-05-25T00:00:00Z
  • Charming cottage with lots of nice touches. Great location and easy walk for ''downtown'' Chestertown shopping, First Friday, and Saturday farmers/craft market, as well as Washington College. Quiet and clean and very convenient.

    Rae2019-05-05T00:00:00Z
  • Allie's bungalow was the perfect place for us to call home while we visited family in Chestertown. The house was very conveniently located next to Washington College and just a few blocks from downtown shops & restaurants. There was plenty of room inside for the 6 of us to sit and talk in the evening. We would definitely stay there again.

    Larry2019-04-21T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Bungalow


    Accommodates

    6


    Bedrooms

    2

    Chestertown, MD, United States

    Popular homes

    Popular homes
    Totally renovated cottage, 5 minute walk from Washington College and downtown Chestertown. The guest quarters include a large open concept kitchen with quartz countertops and new SS appliances, great room with 55" TV, full size LG washer and dryer, 1 BR (master) with queen bed and TV, sitting room/office with queen convertible sofa and TV, 1 bath with travertine tile shower and floating vanity. New HVAC with heat and central air. Includes Wi-fi, Netflix, Amazon Prime TV.
    One on-site parking space. Plenty of parking off-site.
    We are 2 blocks from Washington College and 4 blocks from the center of Chestertown.
  • Beautiful place. It was our first Airbnb experience and it was more than I could have expected!! Loved it!!

    Emilie2019-08-05T00:00:00Z
  • Very clean, great amenities, and great location!!! Would recommend to anyone looking to spend time in Chestertown!!

    Mollie2019-07-28T00:00:00Z
  • Super cute and cozy cottage. The kitchen was spectacular! The one bed was great, the pull out couch was not really comfortable but We did acknowledge that we were sleeping on a sleeper sofa before we showed up, so not fair to take stars away for that. We would definitely rent this place again.

    Natalie2019-07-21T00:00:00Z
  • The Yellow Door Cottage was a great place to stay. Beautiful kitchen and spacious rooms. I ended up staying here with 4 guests and it worked out great! If you are looking for a cozy place to stay, this is it!

    Steve2019-07-14T00:00:00Z
  • This place is amazing! We only stayed the weekend but we can’t wait to come back. Extremely clean, beautiful home. Trendy and right up my alley. All the comforts of home and more! You won’t regret booking here! They have directions and manuals for everything if you need them! The restaurant recommendations in the binder helped out when we got in late one night and wanted to order food! Milano’s Pizza was awesome by the way! Beautifully landscaped outside. Quiet street. Stress free check in! 🌠🌠🌠🌠🌠5 stars

    Kristen2019-07-07T00:00:00Z
  • Beautiful home!!! It was well stocked with all you need for a perfect stay. Stephen was a wonderful and thoughtful host. We will definitely be back again.

    Sarah2019-06-30T00:00:00Z
  • The Yellow Door Cottage is newly remodeled, stylish, spotless & comfortable. The hosts Steve & Noreen are great!! They truly have thought of everything you could possibly need to make it a “home away from home” stay. The unit was nicer than many of the resorts I’ve stayed at and much more affordable.

    Robin2019-06-24T00:00:00Z
  • Great location, amenities, communication, and check-in/out process. Perfect for our college reunion!

    Denise2019-06-09T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Cottage


    Accommodates

    4


    Bedrooms

    2

    Chestertown, MD, United States

    Our pet friendly home is located in a quiet neighborhood centrally located to shops, restaurants and Washington College. It is a 1 story, 3 bedroom, 1 and 1/2 bath with fenced backyard and screen porch. Garage and driveway parks 3 vehicles comfortably.
    Our screened in porch is the perfect spot to sit while your pup enjoys a romp around the fenced in yard. Parking in the 1 car garage is available for your convenience. The drive provides adequate space for 3 cars and the 6 guests our home comfortably sleeps.
  • Exceptionally clean ranch house in a quiet neighborhood. Large kitchen well stocked with appliances, silverware, cookware. Fenced backyard for dogs to play in. Screened in porch is an added bonus.

    Jill2019-11-24T00:00:00Z
  • Place was as described and the location was convenient for our needs (close to some nice restaurants, and not far from the cute "downtown"). Overall, I think this place was a good value.

    Ryan2019-11-17T00:00:00Z
  • Great service. Easy check in. 100% recommend

    Michael2019-10-20T00:00:00Z
  • We have been traveling to Chestertown for the past 6 years while our daughter was going Washington College. The house is only minutes away from the campus by car on a very nice quiet street. The bonus feature for us was the screened in porch off the back of the house so we could enjoy our coffee outdoors in the morning. Susan was very helpful with meeting us as we came in and provided an excellent tour of the property. This will be our go to place from now on when we visit Chestertown!

    Greg2019-10-15T00:00:00Z
  • Our stay at Merry Manor was wonderful. The house is centrally located and is very cozy. Susan was very accommodating and an excellent communicator. My family and myself had a wonderful stay. Highly recommended!

    Justin2019-10-13T00:00:00Z
  • Clean, a nice amount of space, 1.5 baths, a fenced in backyard which was fairly spacious. There's a screen room out back as well. The bed was comfortable. There were towels, utensils, coffee maker (with coffee), fridge, etc. all for our use. Overall, for the weekend, it worked out great for me, my wife and dog!

    Peter2019-09-29T00:00:00Z
  • Perfect space and set up for a quick weekend trip to Chestertown for a wedding. Everything we needed, an excellent value and convenient to the college and town.

    Morgan2019-09-22T00:00:00Z
  • Convenient, comfortable, clean, and well equipped. Great hosts. Would stay there again.

    Ben2019-09-15T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    6


    Bedrooms

    3

    Chestertown, MD, United States

    "The fresh smell of coffee soon wafted through the apartment, the smell that separates night from day." Haruki Murakami "'You can't understand most of the important things from a distance...You have to get close,' she told me all the time." Bryan Stevenson, Just Mercy Freshly brewed coffee, a hot cup of tea, the simple things, invite us in, to "get close." Simplicity pulls us to itself, welcoming us to slowly savor - to sit for a spell - just like at home. Traveling? You're invited!
    4 outside steps lead to our front door, followed by 14 upstairs to Erin's Room. The Queen bed is perfect for a business traveler, or for those looking for quiet and comfort. Erin's Room is in our fully licensed B&B, with top ratings on popular review sites. All federal, state and county taxes are remunerated.
    The neighborhood is quiet, with Washington College being at the end of our street. Downtown and the river are a short walk away.
  • Cheryl is a very welcoming and thoughtful host. Her home is sparkling clean and our room was really comfortable. We felt at home immediately. We will definitely be back!

    Rebecca2019-11-03T00:00:00Z
  • The perfect representation of cute Chestertown

    Jack2019-10-27T00:00:00Z
  • Cheryl was the perfect host!! Her and her husband made me feel right at home with their amazing hospitality! I was in town for work but I truly was sad I had to leave so soon... highly recommend!!!

    Ja2019-10-22T00:00:00Z
  • This is just the cutest little Inn. It’s like staying at a friends house and then some. The little extras like water and snacks are so thoughtful. The rooms are very clean and full of character. And you can’t beat the location - so close to everything. We’ll be back for sure as we plan to visit our niece again at Washington College.

    Nicole2019-09-29T00:00:00Z
  • Cheryl is a gracious host and provides a clean, and comfortable room for her guests in a quiet neighborhood. Is easy driving distance from the Marina and local restaurants.

    Francoise2019-09-28T00:00:00Z
  • I had a very good stay at Cheryl’s place. She was very communicative and friendly, and the room was very relaxing and in a great location in town. Would stay again!

    Emily2019-09-27T00:00:00Z
  • This room is perfectly located walking distance from the University. Clean, quite and friendly.

    Patrick2019-09-22T00:00:00Z
  • Relaxing atmosphere and nice personal touches. Handy to have a small doemmsize fridge/freezer in the room. Hospitable hosts!

    Christina2019-09-16T00:00:00Z
  • Room Type

    Private room


    Property Type

    House


    Accommodates

    2


    Bedrooms

    1

    Chestertown, MD, United States

    In town, overlooking the marina. A beautiful spot!
    Entire two bedroom, great room apartment with loft and balcony. Private entrance.
    Two blocks from town. Overlooks the town’s Marina.
  • Everything at the ‘River Watch’ was better then described. A lovely setting for a girls get together. Never had to get in our cars the whole weekend to explore the town. Will hopefully I sit again.

    Maggie2020-03-08T00:00:00Z
  • Perfect little place with a beautiful view of the Marina. Everything you could ask for in the apartment with really neat little touches. Decorated beautifully, and while quaint, there are plenty of places to find a corner to yourself when you want it. The Grill across the street on the Marina is great, and it’s a super short walk to town square where there are some wonderful shops and restaurants. I highly recommend this town and accommodation. Only negative thing I have to say is we didn’t get to stay long enough.

    Timothy2020-02-09T00:00:00Z
  • This house is quite literally a 3 minute walk from the main street in Chestertown. It would fit 4 people comfortably (1 per bed). The hosts were very kind and friendly and gave great recommendations for the town!

    Sarah2020-01-29T00:00:00Z
  • Great stay highly recommend Casa Carmen and The Retriever only blocks away.

    Sharon2019-12-28T00:00:00Z
  • Perfect accommodations to enjoy all Chestertown has to offer .

    maureen2019-12-08T00:00:00Z
  • Walter was an excellent host, and his property was perfect. Thanks again for a great stay!

    Dave2019-10-21T00:00:00Z
  • Wonderful place to stay! Highly recommend.

    Rachael2019-10-20T00:00:00Z
  • Must be the best Airbnb location I have experienced - right on the small, picturesque harbor. Nice grocery store just three blocks away. No traffic at all. Huge bathroom, cool little loft, high ceilings, extremely clean. There’s no actual kitchen nook, but the fridge, sink and microwave are fine for a weekend stay. Firm, good mattresses, decent cable TV selection, good lighting, plenty of towels. Would go back.

    Tero2019-10-14T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Flat


    Accommodates

    4


    Bedrooms

    3

    Chestertown, MD, United States

    Entire flat4 beds
    RIVER WATCH
    Price:₹15,710/night
    18 reviews
    Superhost
    Location location location! We absolutely love the proximity of our house to campus, the historic district, and the river. Chestertown is charming and there are fun little shops and restaurants around every corner. Our home is cozy and perfect for entertaining. We hope you enjoy it as much as we do!
    Gorgeous late 1800 victorian home renovated with modern amenities and decorated with a beachy-chique vibe! Has great indoor-outdoor entertaining space including a charming front porch, rear deck of kitchen and fully fenced backyard. Room to stretch out in the large bedroom including king & queen beds. Recently renovated throughout include newly refinished hardwoods throughout the home, and tastefully updated baths! Beautifully updated kitchen incl. slate floors, silestone counters & stainless steel appliances. Charming main level include formal dining for 8 w/open living/dining combo perfect for relaxing & entertaining! Located in the Historic district; two blocks to Washington College, restaurants, coffee shops, book store, retail shops, and 5 min walk to Saturday's Farmer's Market and Chester River waterfront! The perfect location for exploring Chestertown, Kent County, Eastern Shore and perfect weekend getaway!
    We are in walking distance to Washington College campus, the downtown coffee and retail shops, the Saturday morning farmers market in fountain park, and the Chester River waterfront.
  • This place was fabulous and if you can believe it, even nicer than the photos! The town is lovely and the house is an easy walk into the Hallmark-Movie-Like neighborhood. The house appears to have been recently renovated and the work is first rate. In addition to being clean and spacious, the decor is really lovely and just modern enough to compliment the colonial style architecture of the house. Parking in the driveway and on the street was plentiful. The neighborhood was very quiet, even though so close to town. We were a group of 7-9 women and we prepared breakfast and dinner each day. The kitchen has very good quality appliances and is incredibly well-stocked, even for 7 foodies! We found everything we needed to put fantastic meals on the table. The 2 1/2 bathrooms, including a powder room off the kitchen, were great and all were spotlessly clean and well-stocked. The towels were particularly wonderful. The bedrooms were lovely, loads of pillows and beautiful bedding, comforters, extra blankets, etc. The mattresses seemed to be memory foam or some hybrid, but all new and comfortable. There were several lovely sitting rooms/areas in the house that were charming and comfortable and the spin around armchairs in the living room were great for movie-watching. We found a jigsaw puzzle and completed it while we were there - and there were no missing pieces! The heating system was responsive and easy to manage. Water pressure was great and hot water plentiful. Ryla sent some information about the town that was spot-on. We tried out the cheese and wine shop, the bakery, and happened to be visiting during Mardi Gras with the parade and gallery crawl. Ryla was also very responsive as we communicated during the days prior to our arrival and was quite accommodating regarding arrival and departure times. In general, this is a lovely place, was very affordable and is in a great location with an excellent host.

    Sandy.Marincic@Hotmail.Com2020-02-24T00:00:00Z
  • Beautifully decorated with great amenities. Perfect location to walk to town and college. Great space and Host was very responsive.

    Sharon2020-02-16T00:00:00Z
  • One of my best AirBnb experiences ever. We rented this house for a work retreat, and it was clean, comfortable, convenient, and just perfect for our needs. Comfortable beds, gorgeous kitchen, delicious coffee...it was just great.

    Adina2020-01-12T00:00:00Z
  • Whether you are visiting Chestertown for an event, Washington College activites or just "getting away," I think you'll enjoy staying at the Duchess of Kent. This home is so inviting. From the convenient entrance hall to the beautiful modern kitchen and cozy living room, this home was exactly what we expected. We were attending Dickens Weekend in town and the location allowed us to walk to the activities, shops and restaurants. We would love to stay again sometime. Ryla was an awesome host who provided us with lots of information and answered all of our questions in a timely manner.

    Karen2019-12-08T00:00:00Z
  • This home is beautifully decorated, very clean, spacious, on a quiet street and only a few steps from historic Chestertown. You will never have to move your car. The home looks exactly like it does on the pictures and is equipped with all the necessities needed for a short or long-term stay. This was our family's "home away from home" for Thanksgiving weekend while visiting relatives in the area. We were 7 adults and there was enough space for time alone or togetherness. We took advantage of the close proximity to town and enjoyed the Christmas tree lighting ceremony with Santa Claus's arrival the night after Thanksgiving. Ryla was very accommodating and quick to respond with any questions before and during our stay. She also provided us with tips on local shops, places to eat and Saturday Farmer's Market. While we're familiar with the area, we also learned of some new ones from her. We would definitely come again and highly recommend it to anyone considering spending some time in lovely Chestertown in Kent!

    Eugenia2019-11-30T00:00:00Z
  • We enjoyed our stay! Will definitely stay again.

    John2019-11-19T00:00:00Z
  • Ryla was extremely accommodating and responsive. Loved staying at her place.

    Katie2019-11-17T00:00:00Z
  • It was a great experience. We needed a place to stay for a wedding at the Brittland Manor. It was close to the venue and to the quaint and charming downtown area . The street was very quiet.

    Kathleen2019-10-20T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    12


    Bedrooms

    5

    Chestertown, MD, United States

    Charming cottage right around the corner from High Street. There you will find restaurants, shops and the best French bakery. Pick up your croissant and coffee, and stroll down to the Chester River.
    Every Saturday there is a local farmers' market in Fountain Park, just steps away.
  • Wonderful home in a beautiful area, everything was easy, accessible, and very clean upon arrival. Would definetly come back again.

    Cameron2020-02-23T00:00:00Z
  • We are in love with Marcy and Ted’s place. It was clean, cozy, and welcoming. The wood stove was delightful. We appreciated the mix of historic and modern-just the right balance! The house was convenient to walking all about historic Chestertown. There’s a well-stocked natural foods grocery close by too. Highly recommend.

    Margaret2020-02-17T00:00:00Z
  • This sweet, historic and charming b& b was a great place for r & r. I found the environment there clean and comfy and cozy and enjoyed being able to walk through the historic neighborhood. This is a wonderful place for a refreshing stay. Well done.

    Lynne2020-01-12T00:00:00Z
  • Marcy & Ted have a nice place in Chestertown, it was clean and well decorated.

    Daniel2020-01-09T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Cottage


    Accommodates

    4


    Bedrooms

    2

    Chestertown, MD, United States

    Upscale 4 bedroom 2700 sf townhouse with beautiful wood floors, and just well-built, great hardware, fireplaces, in a rural town setting. 1st floor queen size bedroom with master bath, great cooking kitchen ( if you ever use it ). 2nd floor master king size 4 poster bed and master bath with a jacuzzi and separate shower. Large equipped granite kitchen, it even has a wine refrigerator, with a beautiful rear garden, in the center of town, you will love your stay!
    5 minutes to Washington College. 98 Cannon St, walk to the Farmers market early Saturday morning in fountain park
    Evergrain Coffee shop has great breve lattes just 5 min walk. LTO great whiskeys, and Chester river riverfront just a few min walk. You can always get in your car and go to Shanty Bar in Tollchester, or go watch a sunset at Ferry Park
  • This house is AMAZING inside! Big, gorgeous rooms, perfect for entertaining or hanging out. Everything is very luxe, and you really feel like you are at a getaway at a five-star hotel. It looks *much* different inside than outside, so don't be deceived by the modest exterior in the photos. The host was communicative, answered all my questions, and made me feel very welcome.

    Hilary2019-11-17T00:00:00Z
  • We were switched to another place next door. It was beautiful and worked for our needs. The house is immaculately clean. It has everything you could imagine you would need. We would definitely recommend and stay again.

    Sally2019-11-03T00:00:00Z
  • Large space; great for a family gathering or big friend group. Loved the kitchen space and deck!!

    Kristin2019-10-27T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    10


    Bedrooms

    4

    Chestertown, MD, United States

    My husband and I, and our friendly Jack Russell are offering part of our home for your visit to historic Chestertown. We offer: Room A: Master bedroom with a queen-size bed and an en-suite private bathroom for your comfort and privacy. Room B: The room is set up like an office with a desk, chair and a full-size bed. If you want to use Room B you will be charged an additional $20. In your reservation select 3 guests to include Room B. Our home is clean, simple, and cozy.
    Room A and en-suite bathroom: All linens and towels included Television with Roku Express with free Netflix Garment rack-hangers and cubie shelves for your clothing and personal items. Alarm clock and charging station for your devices The bathroom has a standup shower. Wifi Internet Room B Desk with a laptop computer and printer for guest use. Full-size bed Kitchen: The use of the kitchen is limited only to: refrigerator, microwave, toaster oven, coffee pot, electric kettle. You may use the screened porch, and breakfast nook for your meals. Easy free street parking is available Please note: our dog is an inside pet. However, he will stay out of your room.
    The home is in College Heights, approximately an 8-minute walk (0.4 miles) from Washington College. The historic downtown area is approximately a 20-minute walk (1 mile). Downtown you can find many small shops, cafés, restaurants, and of course, the Chester River and marina. If you want to venture further away you will need a car. Close by you can explore Rock Hall, a very cute boating/marina community (20-minute drive) with an excellent nature reserve (Eastern Neck Wildlife Refuge) and several restaurants.
  • Sleek, streamlined room and bath appointed very efficiently and thoughtfully. Very comfy bed and adorable dog!

    Lisa2019-12-30T00:00:00Z
  • Martin and Sergio hosted us on a short notice. There place was extremely clean and very nice. We loved their little dog Tony who was quite the energetic puppy! We would not hesitate to book again!!

    Jody2019-11-20T00:00:00Z
  • Our stay at Martin's place was delightful. They are friendly, helpful hosts. Kind and considerate. The place was spotlessly clean, and stylish. And walking distance to the college.

    Patrick2019-11-03T00:00:00Z
  • Wonderful AIRBNB experience in all ways: hosts welcoming and kind, location perfect to visit my son at Washington College and room/ bathroom clean and comfy! Highly recommend.

    Kim2019-10-26T00:00:00Z
  • Room Type

    Private room


    Property Type

    House


    Accommodates

    3


    Bedrooms

    2

    Chestertown, MD, United States

    Historic house in Chestertown renovated to a LEED silver standard, in the center of town. One block from the best Saturday Farmer's Market in Maryland, three blocks from the Chester River and four blocks from Washington College. Well furnished with antiques and fine paintings in keeping with the quality and history of the 18th/19th century house. Gourmet kitchen and family room, 2nd floor bedroom and bath. 3rd floor bedroom similar to 2nd floor. Front porch, back patio , off street parking.
    Located at highest point in historic district and on main street in Chestertown, Maryland.
    Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    4


    Bedrooms

    2

    Chestertown, MD, United States

    Lovely home with great indoor-outdoor entertaining space. Fully renovated 3 bed, 2.5 bath. Top of the line open floor plan kitchen/family room. Located in Historic district on the main street only few blocks from restaurants, shops and river front.
    Combing southern living with the sophistication of London. This is an in town Historic 1880 house that has been expanded and completely renovated. New exterior, kitchens, baths, bedrooms, family room, porches, pergola. Nine foot plus ceilings accented with architectural custom designed molding throughout. Bright southern exposure kitchen with large entertaining cooking area and family room. Granite counter tops in kitchen, hand tiled, Bosch dishwasher, gourmet 6 burner dual fuel Wolf oven and range. Extra large master bedroom with cathedral ceiling – matching cathedral ceiling in master bath. Master bath with custom black and white tile work, twin sinks, marble counter tops/ standard shower/rain shower/body jets/bench and original claw foot tub. Covered porch off of family room w/ipi mahogany deck. Side cedar beamed arbor pergola off of family room with ipi mahogany deck. Detached garage with professionally finished space above – mahogany floors frame the backyard (not included). Brick and stone patio with beautiful perennial garden –to complete this wonderful property.
    Quiet tree lined street - two churches with in one block - library across street. Three blocks to center of town, restaurants and shops. No problem to leave the doors unlocked when you step out.
  • Carey’s home in Chestertown is stylish, well located and has all the comforts of home. The kitchen is fabulous; the beds comfortable - essentially this home represents what Air B&B should be providing its clients. I’ve stayed here multiple times and it’s always a pleasure any time of year.

    Dan2020-01-10T00:00:00Z
  • Carey's house in Chestertown is a stylish home - it makes Chestertown an excellent experiennce.

    Dan2019-12-07T00:00:00Z
  • Carey's home is beautiful and the location is great for walking to explore all places in downtown. I would highly recommend.

    Kenzie2019-10-20T00:00:00Z
  • Third time staying here and it gets better and better. Location is perfect, and the house is like entering a museum.

    James2019-09-22T00:00:00Z
  • Beautiful home and great location

    Linda2019-09-15T00:00:00Z
  • A beautiful place to stay plenty of room and some. Meticulously clean .

    Kirk2019-09-09T00:00:00Z
  • Love this house! Fabulous kitchen. Beds were luxurious!

    Becky2019-08-26T00:00:00Z
  • Carey is a wonderful host with a beautiful home. The location is perfect to town. Easy walk to the shops, restaurants and the river.

    Betty2019-05-27T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    5


    Bedrooms

    3

    Chestertown, MD, United States

    This century-old three-story home is in the beautiful historic district of Chestertown, which sits on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue. Heron Point is a short drive down Campus Avenue.
    56th Annual George Washington Birthday Ball - February 22 WC Spring Break - March 9-13 Washington College Piano Festival - March 28 100 Proof Annual Juried Student Exhibition - April 4-10 Chestertown Tea Party Festival - May 22-23 The National Music Festival - May 31 - June 13 Stay with us while visiting at Heron Point. The bright, spacious guest suite is on the 3rd floor. It includes a beautiful, large bedroom with a king-size four-poster bed and comfy memory-foam mattress, a separate sitting room with a flat-panel TV and a trundle daybed for up to two extra guests. The private full bath has been newly-remodeled. Fix yourself a cup of coffee in the kitchen! Our guests can choose to unwind and drink their coffee on the 1st floor screen porch. Ask us about special arrangements for: - Traveling Nurses (we're one block from the hospital) - Visiting Faculty (we're right across the street from the college) - Your 4-legged family members! We charge $15 a night for each pet (crated only, please!). If you want to bring yours, let us know and we'll send you a special offer to include them! - Unique circumstances
    The Washington College Campus Green is right across from our front yard, and a four-block walk will take you to Fountain Park and the shops, bars, and restaurants in historic Chestertown. Try The Blue Bird up the street for great crab cakes or Tuesday Wing Night, or the Kitchen for Thursday night Martini Night (or a delicious dinner!). Visit Play It Again Sam's for coffee and lunch. Check out more in our guide book!
  • Spacious, beautifully decorated and warmly inviting, Jim & Gale’s wonderful Victorian home is perfectly located in Chestertown. Their superb hospitality and kindheartedness made our very comfortable stay a genuinely delightful holiday treat!

    Johnny2019-12-01T00:00:00Z
  • What a lovely stay in a great location. Jim and Gale are wonderful hosts. The suite is beautiful and comfortable, we loved it. We enjoyed being able to walk across the street to see a play at Washington College, walk or drive to the farmer's market, or sit on the lovely porch at home. Gracie the pup is an Airbnb bonus.

    Becky2019-10-27T00:00:00Z
  • Wonderful clean, cozy, and private space for my family of four. The pictures are accurate in terms of size and cleanliness of the space. Jim and Gale are the perfect hosts. Communication was easy and everything went great. No complaints. Will definitely contact them again the next time we visit the town.

    Michael2019-10-20T00:00:00Z
  • Great place to stay! Rooms were in A++++ condition! Beautiful place. Gale and Jim were friendly and thoughtful!

    Ivan2019-10-13T00:00:00Z
  • Room Type

    Private room


    Property Type

    House


    Accommodates

    4


    Bedrooms

    2

    Chestertown, MD, United States

    Located in historic district of Chestertown. One block from the Chester River, walking distance to bakery, restaurants, coffee shops, book store, retail shops and Saturday's Farmer's Market.
    Spending time downtown without having to drive again until you leave is a plus. Everyone loves staying downtown if you like people. Guests will have access to restaurants, bakery, shopping, Saturday Farmer's Market, Garfield Center for the Arts, Good walking paths. We can be as flexible as our guests ask for. We love being able to step out on the sidewalk and always see someone we know who is walking their dogs, babies, or just a stroll down to the foot of the street to the Chester River. Wilmer Park is right around the corner where you can sit on park benches and watch the activity on the river and read or just enjoy the scenery.
    We love being able to step out on the sidewalk and always see someone we know who is walking their dogs, babies, or just a stroll down to the foot of the street to the Chester River. Wilmer Park is right around the corner where you can sit on park benches and watch the activity on the river and read or just enjoy the scenery.
  • If you are visiting Chestertown, this is the ideal location. Walking distance to all area shops and restaurants. Phyllis and Pere leave special touches. They are great hosts. Hope to be back next year!

    Patricia2019-12-08T00:00:00Z
  • We had a wonderful getaway weekend and Phyllis and Pere were the most gracious hosts! The house was so comfortable and I wish we could have relaxed longer. The perfect spot for a weekend away from home!

    Kristen2019-11-17T00:00:00Z
  • Phyllis and Pere have a special home that is exceptionally well located in the center of Chestertown, Maryland. You can walk to anything you want to do. Phyllis and Pere are extremely responsive and go out of their way to make your stay perfect. They provide bottled water, snacks and a beautifully appointed home that is a rare combination of elegant and comfortable. Add to this a lovely manicured private outdoor space and you know you have hit a grand slam. Check in was simple and they were very flexible about our late check in and equally flexible about our check out. If you are heading to Chestertown and want a well located lovely place to relax then look no further then this special space.

    Audrey2019-11-03T00:00:00Z
  • Lovely house in such a cute little town. Highly recommend!

    Betsy2019-09-29T00:00:00Z
  • Phenominal location in Chestertown - right in the thick of historic center and shops! House is a perfect getaway. Back yard is a quiet beautiful space. Gardens are exceptional too! Hosts are as welcoming as could possibly be.

    Timothy2019-09-22T00:00:00Z
  • Phyllis and Pere were amazing hosts. Their home is beautiful, clean, filled with everything you need, and in a great walkable location. Phyllis and Pere were both so easy to work with, and offered to provide transportation for the wedding we were in town for. Very wonderful hosts. This cute home is a little gem, and perfect for a weekend getaway.

    Meg2019-09-15T00:00:00Z
  • Thanks Phyllis and Pete for a wonderful stay in Chestertown! The house and location were perfect!

    Michelle2019-09-08T00:00:00Z
  • Phyllis and Pere are the most gracious hosts. They were very kind when we were late to check in due to traffic, they went above and beyond with snacks, water and wine available, and gave us a great tour of their beautiful home. It’s a stunning house with plenty of room and a backyard oasis that is so peaceful. The home is just steps from the Main Street and farmer’s market. I would love to stay at their home again. Thank you both!

    Madeline2019-09-01T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    4


    Bedrooms

    2

    Chestertown, MD, United States

    This 4 bedroom, 3 bath waterfront home is a terrific place to enjoy time with family and friends. This home has amazing amenities; from the stylish updated renovations and furnishings (some antiques), the screened porch, patio, fire pit, hot tub (colder months), sporting equipment, to the spacious, comfortable, indoor & outdoor gathering spaces. The kitchen is well-appointed with gourmet appliances, and plenty of hosting and culinary supplies to savor wonderful meals together at the house.
    Our waterfront property is located within a mile's walk or bike ride to downtown Chestertown. This home has a mix of antiques, and comfortable new, stylish furniture that today's vacationers want. The house was renovated with the most impeccable taste (we were fortunate to buy it this way). It has just about everything you would need to enjoy time together with your family and friends. From the huge screened porch with amazing new, chic outdoor furnishings (including an 8 foot farm table for crab picking or fancy dining), to a patio, hammock, canoe, paddle boards, fishing rods, crabbing net and trap, along with 4 adult bikes, this home will prove to be one of your family's more memorable experiences together. October through the end of April you can enjoy the use of the hot tub and fire pit. If you want to just relax indoors there is a large screened tv with a big (PB) sectional and chair to gather together. In the colder months, you can also enjoy the wood-burning fireplace (next to tv). The bigger master bedroom with oversized bathroom is located on one side of the house, while 3 other bedrooms with 2 bathrooms (one in the original master) are located on the opposite side.
    I have really nice neighbors. The street and the homes are all charming. As there are not many homes on the street, it can be a good area for kids to ride their bikes.
  • We have stayed at this beautiful property for several years and it has become an annual tradition we look forward to enjoying. The home is as comfortable as they come and the location and view cannot be beat. Truly a gem of a place. Highly recommend!

    Michele2019-11-23T00:00:00Z
  • Beth's place was beautiful! The outdoor space was perfect for hanging out during the day and being right on the water was a huge plus. The house itself was clean and had everything we needed. I would definitely stay here again.

    Katie2019-09-15T00:00:00Z
  • A great place for a family getaway !

    Jim2019-08-25T00:00:00Z
  • Just book it. Don’t let this one get away. The home was a perfect space for my extended family of 9. Beautiful house, great kitchen facilities, outstanding screen porch, huge backyard and the dock with paddle boards and canoe. We absolutely loved our stay! The pictures do NOT do it justice.

    Linda2019-07-26T00:00:00Z
  • I will tell you , Beth’s home will not disappoint! Absolutely wonderful. Everything you could possibly need and want. The river is wonderful to be on, and the ducks adorable.Thank you for your hospitality. Gen Pierce

    Gen2019-06-26T00:00:00Z
  • The house is beautiful with ample space and tons of light, and in the most perfect location - right on the water and near town. The backyard is perfect for relaxing with friends or family. There are lawn and water games, a hot tub, fire pit and a hammock that make it the perfect little getaway.

    Sarah2019-06-09T00:00:00Z
  • We rented this lovely home for our son's graduation from Washington College. It could not have been any nicer. We enjoyed the river and just relaxing on the screened porch. Our two younger children really enjoyed the paddle boards and fishing off the pier. So close to downtown and the college. It was a special time that we will cherish always.

    Lori2019-05-20T00:00:00Z
  • We had a lovely time at Beth’s place. Based on the listing, we came in with pretty high expectations, and were still absolutely blown away by how beautiful this home is. The inside area was clean, spacious, and well appointed. On the rare occasion that the entire group was indoors, we never felt like the space was cramped. We spent most of our time enjoying the outdoor area. The views were absolutely magnificent. We thought we might have to take the canoe onto the river to enjoy the fishing but there was plenty of room on the dock which extends deep into river, and we caught tons of catfish and white perch! We took the canoe and paddle boards out a few times, and the floating dock made it easy to enjoy the water activities. When we weren’t enjoying the water, we were lounging by the fire pit or the hammock. Needless to say, we had a blast at Beth’s place and I’m glad she’s made her beautiful home available for bookings. I hope we can come back!

    Eileen2019-04-24T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    8


    Bedrooms

    4

    Chestertown, MD, United States

    A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet kitchen, two porches, antiques, rugs, and several writing spaces. Dual zone HVAC, washer & dryer, high-speed internet. Plenty of on-street parking.
    A newly renovated Victorian with quiet bedrooms, a spacious living/dining area, gourmet kitchen, and access to a porch, sheltered garden and ornamental pond. Garage in the carriage house with space for two vehicles and electric vehicle charging.
    The whole of downtown Chestertown and its waterfront is easily accessible by foot, including several restaurants, gift shops, food stores and a delightful bakery/cafe.
  • This is a great house that is walkable to all the shops and restaurants of charming Chestertown. Roland is a great host, the house was clean and convenient and we would definitely rent it again.

    Kay2019-12-08T00:00:00Z
  • Charming home on a quiet street yet a convenient walk to town.

    Laura2019-11-03T00:00:00Z
  • Great home!

    Isabella2019-10-20T00:00:00Z
  • Great location and great host. Very responsive and accommodating. Was great to allow my family to all stay together while in town for my sons wedding.

    Charles2019-09-29T00:00:00Z
  • This home is an amazing blend of an old Victorian and architecturally aesthetic renovations. The beds are comfortable and the bathrooms, as the whole home, is spotlessly clean. It is the perfect get-away within walking distant of downtown, the water front and the Saturday farmer's market! We highly recommend this home and will be back.

    Joyce2019-08-12T00:00:00Z
  • Great place located in the heart of Chestertown, Md . We were a group of 8 that spent the weekend to participate in the "Swim for life- 2019" event in the Chester river. Ronald is great and responds quickly. He let us know in advance of the local restaurants and community, and that oven was not working so we are able to plan ahead. Having said that, since we had our meals at the house, it would have been better to have a functional oven:) We had a great time and would definitely come back next year. Thanks, Adriana

    Adriana2019-07-14T00:00:00Z
  • This place is in an awesome location. Roland is an excellent host and is very quick to respond! We would definitely stay again.

    Camille2019-06-09T00:00:00Z
  • Great location. Easy walk to town. On great quiet private street. Very responsive host. Good amenities at the house. Had issue with burned out light bulbs, host resolved very quickly.

    Susan2019-05-10T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    9


    Bedrooms

    3

    Chestertown, MD, United States

    Mid-Century Modern decor thru-out this turn of the century home. Renovated in Fall of 2017 and decorated with attention to detail. For groups up to six. We have recently remodeled UNIT TWO which is the lower unit. These can be rented separately or together with locked door connecting both units. Located 1 1/2 blocks from Washington College and downtown. Early check-in and late check-out available. Front porch adds to cozy charm.
    We want you to enjoy our second home as if it was yours! Wifi, keurig, a well appointed kitchen, extra pillows and blankets. We can arrange for chefs, daily cleaning, just ask and we will see what we can do. Because it is our second home you can check in as early as you like and check out as late as you would like. There is a large foyer with staircase to second floor. Three large bedrooms with new bedding and mattresses. Renovated "save the pink" bathroom with new surround tile, bathroom floor and toilet. Two blocks from Washington College and two blocks to High Street (main street in town), few blocks to Chester river. Perfect weekend getaway only 1-1/2 hours from Washington, DC.
    Fabulous location two blocks from Washington College, two blocks from Main Street in town with quaint shops and restaurants.
  • This is a great place. My family and I enjoyed it and would stay again.

    Victoria2019-09-08T00:00:00Z
  • Lee's house was incredible - we rented both the top and bottom unit for a weekend with a group of 10+ people. Lee was extremely responsive and easy to communicate with. She provided a ton of great tips and let us know we could reach out with any questions or concerns. The house had ample room for 10 people and was AMAZING. Not only what we expected - easy check in, beds, towels, clean, etc., but the most unique house any of us have ever stayed in - Lee clearly put a ton of effort into renovations and it showed! The home was beautifully decorated and a joy to stay in. If we are ever back in Chestertown we would book this house again without a second thought.

    Katie2019-09-01T00:00:00Z
  • The Patriot House is a unique combination of reteo and contemporary decor with a colonial feel. We loved our stay and were within 30min of lots of bay area restaurants and activities.

    Michael2019-08-04T00:00:00Z
  • Clean, great location, and super cool. Just as described! And great host as well.

    Jacqueline2019-06-16T00:00:00Z
  • Lee's house was the perfect spot for our family-weekend in Chestertown. The location was ideal... quiet, but still an easy walk downtown. The apartment was charming and offered ample space for our group (4 adults, 2 children & a toddler). Highly recommend!

    Levi2019-05-27T00:00:00Z
  • This is a gorgeous apartment, makes you feel at home. Lee is very helpful in responding to my questions. I would definitely recommend this house to my friends.

    Sy-Shin2019-05-12T00:00:00Z
  • We had a great time at Lee’s place. It was incredibly clean and streamlined. The layout was great and good for relaxing in the living room and dining area. Location is absolutely perfect for walking around chestertown and checking in couldn’t have been easier !

    Caroline2018-10-28T00:00:00Z
  • Lees place was clean, easy to check in and out and a great place to stay for the weekend. Will for sure stay again while in Chestertown!

    Kailey2018-10-21T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Flat


    Accommodates

    6


    Bedrooms

    3

    Chestertown, MD, United States

    Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!
    Private cottage right on the Chester River. Sleeps 8-14. Private dock with plenty of water activities. The shaded flat yard leads to the river and the private dock where you can enjoy your coffee, watch osprey, eagles & heron, enjoy fishing off the 100’ dock, swim in the Chester river and launch kayaks and paddle boards. The southern exposure welcomes spectacular sunrises and sunsets. Located close to both Chestertown and Rock Hall, it is an ideal gathering space for families and friends with many activities available in the area. By boat, this property is located past Chestertown historic town on the left after clearing the Chestertown bridge. There is a boat launch in Chestertown or two house-down the road and a boat slip available at the house. Contact us regarding water depth if you plan to bring your boat. For outside gatherings, there is a large deck and a nice flat lawn leading to the water with tables for dining under the shade of a magnificent magnolia tree and Adirondack chairs and sofa to take a nap by the water or roast marshmallow on the firepit. For cooking, you will love our renovated kitchen with single oven, dishwasher, and fully stocked with dishes and utensils, including toaster and coffee/tea bar. You can also cook outside on our gas grill. The kitchen, dining room and living room are all open floor plan so you can enjoy family time and amazing river views. The kitchen and living room feature an oversized French door window that opens directly onto the deck and easily walk out to the lawn and the river. For relaxation and amenities, we have a fantastic living room and dining area with water views, full size washer and dryer, wifi, books, games and more! The TV room with its large wrap around sofa (with a queen size pull up sofa too) is perfect to play Xbox or watch old movies. Note there is wifi but no cable TV provided. Plenty of old DVDs available but trust me you will not have time for TV, this a place to disconnect from technology! The river is your entertainment. We also have an outdoor fire pit and indoor fireplace. We provide kayaks, paddle boards and a floating pad for you to enjoy the warm and safe waters of the Chester river. You will also find a ping pong table, soccer nets and badminton. Bring your own fishing gears to fish directly from our private pier! Four large bedrooms, plus two bonus rooms, plus one bunk room for an extra 6 kids! That’s a lot of sleeping room for everybody to have their own space!. Two bedrooms (double & Queen beds) on the main floor share a bathroom with shower/bathtub combination. A bonus room on the main floor is the lovely sunroom with a single day bed. One of the best place to wake up in listening to birds and nature around you!. The second floor has two large bedrooms with two single beds each that can be pulled together as needed. The rooms share a hall bathroom with a double vanity and a shower stall. Bonus room on the second floor is a little kids rooms under the roof that is a lovely spot for toddlers to play and sleep. It has two mattresses for extra sleep over (no AC). Finally, if that's not enough beds or if you wish to keep all those teenagers in a separate wing! the “bunk bed” room on top of the garage awaits! Easy access through the attached garage, the room is carpeted, has window AV and can sleep 6 people. That room has an easy walk down access to the mud room bathroom with its own shower. Linens (bed sheets, bath towels and hand towels) are provided with the rental contract. This is a wonderful house for children of all ages, but please be aware that the access to the water and the dock is not gated. Pets are welcome but be aware that the yard and the water access is not gated and open to adjacent yards. This is a very dog friendly neighborhood, so your dog must be ready for lots of doggy social times! The property is 5-8mn drive to Chestertown. If you're a history buff, fond of cobblestone streets and gas-lit lanterns, you'll love Chestertown. Founded in 1706, it was named one of Maryland's six "royal ports of entry" in the 18th century. Shortly after the Boston Tea Party, Chestertown citizens resolved to prohibit buying, selling, or drinking tea, and they were even said to have held their own tea party on the Chester River. Besides its active history, the town has many amenities and activities, and with its idyllic location and natural beauty, you're bound to love your time in Chestertown. It is a year-round, striving and quaint town with an active community of mixed age thanks to Washington College students and an ever-growing population of baby boomers who elected to retire in this wonderful community. This is one of these towns where you can still find a music store, an old fashion book store, a bakery (best baguette and croissant outside of France…and I am French!) and a Wine & Cheese store. The town is also home to several quaint cloth, craft and gift stores and wonderful restaurants. Chestertown is also known for its Art galleries and the Garfield Theater where you can catch a play almost every week-end. Saturday is market day in Chestertown with over 50 vendors offering farm fresh products. The newly renovated Marina down the main street is also an active part of the town with water front activities. The town has many festivals include HP, Tea Party, Downrigging, Jazz festivals. If you want to catch a movie there is also a great renovated new movie theater. But while Chestertown will enchant you for its old stones and quaint atmosphere, it is still very easy to access modern necessities with Acme, ACE, Walgreen, hospital, etc. We are also 20 minutes from Rock Hall & 45 minutes from Annapolis and St Michaels. 35 minutes from premium outlets in Queenstown. Great location for couples' retreat, a girls' getaway weekend, family reunions with kids or grand kids or home base while visiting your Washington College student. It is truly a tranquil oasis that invites you to leave your stress at the door and enjoy nature's
    Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    10


    Bedrooms

    5

    Chestertown, MD, United States

    Welcome to the Patriot House in Chestertown, Maryland. We recently renovated this beautiful home with a "Mad Men" Mid-Century modern vibe throughout. This is Two Units that combine together with connecting door for a total of 6 bedrooms and 3 remodeled bathrooms. You are renting entire first and second floors. Two kitchen and two living rooms. Wide front porch is perfect for cocktails or morning coffee. 2 blocks to Washington College and Downtown. We do not rent to undergrad students.
    Welcome to the Patriot House in downtown Chestertown, Maryland. We recently purchased and renovated this beautiful home with a "Mad Men" Mid-Century modern vibe throughout. This is Two Units that combine together for a total of 6 bedrooms and three remodeled bathrooms. Enter into the two story foyer and gorgeous stairway to second level unit. You are renting entire first and second floors. Upstairs there are three large bedrooms with two queens and a king plus one "Save the Pink Bathroom" which keeps it's quaintness while being remodeled. Comfortable living room includes martini bar and modern art. Wonderfully tucked away reading nooks and seating areas. Well appointed kitchen with open shelving invites a dinner party and dining room seats 6-8. Lower unit with connecting door has three large bedrooms with two king beds (one with additional twin in it) and a queen bed, plus two remodeled bathrooms. There is also a large living room with sectional sofa and seating area plus mid-century modern kitchen. Wide front porch is perfect for cocktails or morning coffee. Two blocks from High Street with restaurants, bars, distillery, wonderful shopping and Saturday farmers market and two blocks to Washington College.
    Two blocks to Washington College and two blocks to main street of Chestertown
  • This place was loved by everyone in our group. A fun, well-appointed space. Very nice bedrooms and common spaces. Well though-out interior design.

    Maria2019-11-29T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    13


    Bedrooms

    6

    Chestertown, MD, United States

    Bright and spacious manor house room with 5 large windows overlooking the front and side park.
    Spacious room on the 2nd floor of an 1860 Plantation House
    20 acres of lush gardens and woods one mile from historic Chestertown.
  • This trip was absolutely amazing, we couldn’t thank you enough for such a wonderful place to stay! This was our first time staying at a bed and breakfast, and our experience at the Brampton Inn was above and beyond our expectations! Everyone we encountered on the property were so very nice, polite, and accommodating. The property itself was beautiful. It was definitely one for the books and we are already wanting to come back!

    Sabrina2019-06-24T00:00:00Z
  • Room Type

    Hotel room


    Property Type

    Bed and breakfast


    Accommodates

    2


    Bedrooms

    1

    Chestertown, MD, United States

    Quiet cottage next to Heron Pond adjacent to the Chester River. One mile from the historic town of Chestertown and 1/4 mile to the Country Club.
    The cottage sits on a quiet pond with ample yard to run and play. There is a brick patio with a picnic table to enjoy the outdoors. The kitchen is fully stocked with everything you should need to make your stay pleasant and relaxing! There is a washing machine and dryer in the cottage for your use during your stay.
    We are in a quiet neighborhood on the Chestert River. There are lots of great routes to walk, run or bike! There is a great farmers market on Saturday morning for fresh produce and crafts. There are four kayaks which may be used. Life jackets are supplied and are necessary!
  • Super close to Chestertown and a short walk from the water, this made for a perfect weekend getaway.

    John2019-10-06T00:00:00Z
  • Amazing hosts, the best AirBnb dog ever, and a lovely cottage. Great location, lovely indoor and outdoor spaces, chickens, river view, and kayaking. Loved our stay, and cannot wait to get back there.

    Becky2019-09-22T00:00:00Z
  • Clean and great spot!

    John2018-10-28T00:00:00Z
  • Just a described. Very much enjoyed this little cottage. Hope to visit again sometime in the future.

    Mike2018-09-30T00:00:00Z
  • This was my first time using air b&b and I must say that Jennifer’s cottage far exceeded my expectations it was super clean and tidy and very home like. Everything was very well organized. Aside from all that it is a very serene environment on her property. I would highly recommend her place for any occasion. Thank you!

    Nick2018-06-03T00:00:00Z
  • Wonderful stay! Lovely cottage with everything we needed. My kids loved the chicken coop and fresh eggs in the morning. One thing to be aware of- the oven/range run cool, so if you are going to cook, prepare for a longer cooking time!

    Michael2018-05-28T00:00:00Z
  • We enjoyed our stay at Jennifer's home - great location, and everything we needed was right there!

    Peter2018-05-21T00:00:00Z
  • We love the backyard, chicken coop, & pond!

    Colleen2018-04-02T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    Cottage


    Accommodates

    4


    Bedrooms

    2

    Chestertown, MD, United States

    Home away from home. This beautiful Victorian, it's a vacation in it self. like having your own bed and breakfast to yourself. Walking distance to town and Washington College.You will love this house, you will not want to leave.
    Please leave sheets and towels in the big gold basket before checking out. No need to wash them. Thanks
  • Beautiful historic home in the heart of storybook like Chestertown!

    Mark2019-10-20T00:00:00Z
  • Great house in a great location! Everything was perfect.

    Justin2019-09-22T00:00:00Z
  • This is the most beautiful (and cleanest!!) place I have ever stayed in. Pictures and words do not do it justice. I never wanted to leave and I hope to come back soon! Thank you Margaret you are an amazing hostess and your place is #1.

    Zuzelle2019-09-01T00:00:00Z
  • Great place to stay!!! It was so clean, comfortable and charming. Highly recommend. Margaret was a great host!

    Mary2019-08-04T00:00:00Z
  • Great home. Clean, well maintained, and in a great location. Peggy was great.

    John2019-07-28T00:00:00Z
  • Great place to stay!

    Nicole2019-06-23T00:00:00Z
  • Great home, central location, comfy beds!

    Caitlin2019-06-16T00:00:00Z
  • The Home Away from Home is just that. The house is spacious and comfortable with many spaces for lounging and conversing. Its location in Chestertown is perfect. Be aware there is only one full bath, and you may need to do without some little things, like an iron and can opener. Otherwise, the house is well stocked and a good place for a getaway from city life. Peggy is a great communicator and made the check-in super easy. Thank you!!

    Gretchen2019-06-02T00:00:00Z
  • Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    5


    Bedrooms

    3

    Chestertown, MD, United States

    Grand 3rd floor manor house room with 5 large windows and views of the front park. Queen bed.
    The large and airy bedroom is situated on the third floor in the manor house of the 1860 National Register Brampton Bed and Breakfast Inn. The spacious room has an en-suite bath room with a shower.
    The inn is located one mile from historic Chestertown, home of Washington College.
    Room Type

    Hotel room


    Property Type

    Bed and breakfast


    Accommodates

    2


    Bedrooms

    1

    Chestertown, MD, United States

    A full a-la-carte breakfast is included! Elegant 2nd floor room in the 1832 manor house wing is reached through its own steep, private staircase. Please note: This room is not suitable for very tall guests or those having trouble navigating steep stairs.
    The large and airy guest suite is situated on the second floor up a very steep and narrow staircase in the manor house of the 1860 National Register Brampton Bed and Breakfast Inn. This room is not recommended for folks who have trouble with stairs. The room has an en-suite bath room with a double spa shower.
    The inn is located one mile from historic Chestertown, home of Washington College.
    Room Type

    Hotel room


    Property Type

    Bed and breakfast


    Accommodates

    2


    Bedrooms

    1

    Chestertown, MD, United States

    Solid renovated house great location in the center of town
    Surround yourself in history. 3 bedrooms, sleeping for up to beautiful kitchen with concrete counter, beautiful refinished hardwood floors, brick fireplaces.
    Walk to the Garfield Theater, the High St waterfront, 98 Cannon St, 1 block walk to Evergrain and Massoni Art Gallery, 2 to Fountain park and the Farmer's market.
    Room Type

    Entire home/flat


    Property Type

    House


    Accommodates

    7


    Bedrooms

    3

    Chestertown, MD, United States

    "The ache for home lives in all of us. The safe place where we can go as we are and not be questioned." Maya Angelou Whether sinking into the overstuffed chair with your feet tucked up under you or relaxing, curled up on the spacious bed under a comforter, the spaces at Simply Bed & Bread are satisfying, safe and well, maybe even soul-warming. A guest said to us that staying here is "like going home" (in a good way), so it could be that Emily's Room might be just what you've been looking for.
    Size of bed: California King. Location: 2nd floor, up the stairs. An easy 10 - 15 min. walk to downtown; 2 - 5 min. walk to WAC campus. Don't miss the tea pot in the dining room as you arrive through the front door. There's nothing like a soothing, hot cup of tea to warm your hands and calm your mind as you recover from a long drive filled with the stress of traffic and traveling. If you're traveling with other guests, you might also want to book Erin's Room ("Another Simple Stay").
    Washington College is at the end of our street, with downtown and the waterfront being just a short walk away. Let the quiet parts of our little town draw you in... Perhaps you've been lulled into the magic of the National Music Festival where music saturates our town for 2 full weeks each June. Maybe it's just a get-away that is bringing you and you're looking for a simple stroll down to the Farmer's Market on a Saturday morning. Have you had a spell placed on you, bringing you to the Harry Potter Festival? Or maybe you've heard about one of our annual festivals, downtown or on the waterfront. Whatever the reason, Chestertown's pull will satisfy and draw you back. Again, and again.
  • Very comfortable guest room, in a charming house, very well placed for visiting the region. Close to Washington College and the center, within walking distance. Cheryl and David offer you a warm welcome!

    Marc2020-01-22T00:00:00Z
  • What a wonderful Airbnb! Steps from Washington College. So cozy that we checked in and didn’t leave our room until the next morning. Thank you for your gracious hospitality.

    Tiffany2019-11-14T00:00:00Z
  • Very charming and clean space conveniently located to village of Chestertown. Host communicated very well, was warm, welcoming and friendly.

    Lisa2019-11-04T00:00:00Z
  • I had a great, but short stay at Cheryl’s B&B. I was in town for a big race and needed a quiet and close place to stay. It was absolutely perfect

    Steve2019-09-28T00:00:00Z
  • We had a fantastic stay at Cheryl’s place. Our room was impeccably clean and had many thoughtful touches. She and her husband graciously helped us out with several last minute items that we had forgotten! We stayed one night to attend a nearby wedding, but after staying there, we would consider coming back for a weekend just to enjoy the quaint town.

    Yun2019-09-01T00:00:00Z
  • This was my first AirBNB experience, and I really didn't know what to expect. Cheryl couldn't have done a better job as my host. Literally....5 stars across the board. Her house was really great, the room was really charming, the bed was comfortable, everything was really clean, and Cheryl was incredibly welcoming and accomodating. What a great experience! ~KP

    Kevin2019-08-31T00:00:00Z
  • What a great location it is walking distance to town for the farmers market on Saturday, shopping and restaurants. Emily’s room is spacious, comfortable and very clean. I loved having a fridge in the room as well as a pitcher of water in the fridge upon arrival. Cheryl and David were such a pleasure to spend time with chit chatting about everything over coffee!! Thanks for a great stay!! I will be back and would recommend to everyone!

    Karen2019-08-18T00:00:00Z
  • Just genuinely good, kind-hearted people. I can't recommend a stay here enough. Cheryl and David went out of their way to help me out during my brief overnight stay and they made everything such a breeze! Super simple check-in and out, very communicative, easy (free) street parking (town-wide) and just a lovely home in one of the most charming Eastern Shore towns. I stayed in "Emily's Room," and it was incredibly comfortable. Coffee was ready and waiting on the dining room table first thing in the morning! I would certainly stay again!

    Casey2019-08-14T00:00:00Z
  • Room Type

    Private room


    Property Type

    House


    Accommodates

    2


    Bedrooms

    1

    Chestertown, MD, United States

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