Find Places to Stay in Chestertown on Airbnb

Extremely convenient to town, great walking for dogs, and very private space with separate entrance and lovely view of the river. Highly recommend.

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!

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

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.

A beautiful spot to relax and a great little historic and dog- friendly town! Perfect for a weekend get away.

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

This place was great!

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.

The place is close by to everything I'd need, but also quiet. It was also very clean and well-stocked.

Such friendly service and kind hospitality from hosts. The location is wonderful and convenient.

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.

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!

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!

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.

Spacious and clean one bedroom apartment in downtown Chestertown. We very much enjoyed our stay.

Sarah’s place was amazing! She’s an amazing host. Would stay here again.

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.

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!

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.

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.

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!!

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.

We enjoyed our stay in this clean, comfortable, historic house!

Franna is an accommodating host. Her place was charming and great location in town.

This Airbnb was very clean and tidy and had everything I needed. Easy access to wifi and easy walking distance to downtown!

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

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.

Lovely space on a quiet street. Jan met us and made sure we had everything we needed. Fluffy towels and comfy bed. Would recommend!

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.

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.

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!

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!

Meghann is an AirB&B expert. I have never see so many extras and amenities. This place has EVERYTHING. Super clean and location close to town. Had a great time with the family and pups.

The house was clean, comfortable, and well appointed. I would happily stay there again if I were visiting the area. Meghann was a great host.

Great place! Great location!

We had a great time on our trip to Rock Hall. Meghann’s house was beautiful, well stocked, and was exactly what we were expecting. The only complaint I have is that the upstairs room gets very hot because there’s only one vent for the entire room. Luckily, it got cooler at night and we were finally able to cool off the room quicker. Other than that we have absolutely nothing negative to say. She stocked the home with many green earth-friendly products, which we thought was a really nice touch. I would definitely stay in her home again.

This is a very comfortable home. It has a great layout and was equipped with everything we needed. The location was perfect - walking distance to many of Rock Hall's attractions. Meghann was extremely helpful and responded quickly.

Amazing house in an excellent location. Super clean, great communication! I highly recommend!

Great location and very clean.

We loved staying at Meghann’s place. ESP loved the lotion and soaps. Very comfortable space! Thank you!

The cottage is just perfect. You can see the water, the sunset and sunrise views are amazing. It's far enough away to feel secluded, but not isolated. The loft is adorable and the other bedrooms were just the right size for us. And the bathroom tub!! Gorgeous and luxurious with the walk in shower that provides practicality. Just lovely. Kitchen had everything we needed and then some, eating area was big enough to play a board game and the sitting area was cozy. Everything in the experience was easy and pleasant from questions before booking to departure. Will definitely be looking to come back.

We very much enjoyed our stay! The cottage is cozy and comfortable. It is a little rustic in style but has all the creature comforts you need. The kitchen is usable and four can easily sit at the table. In addition to the two bedrooms, someone could sleep in the loft as well as on the couch in the main room. There is one TV in the master bedroom. There is a direct water view although it is past another house and some trees. The best spot to see the water from inside is from the loft where we lounged in the morning. If you want to really see the bay, a short walk takes you to the edge of the cliff where there are some benches. We enjoyed sitting there (with some folks from the neighborhood) and watching the sunsets. In less than 20 min you can be in chestertown, rock hall, or fairlee creek.

Awesome place on the bay

Very comfortable cottage, and great location for getting to and from all the nice stuff around the Bay. Francesca was great to work with and has clearly made an effort to make the space a pleasure to be in. It is as small as it looks, but with just two of us there it did not feel cramped.

Perfect secluded cottage with great sunsets. Close to Rock Hall, Chestertown and Eastern Neck wildlife refuge. The place to go if you need to unwind and relax. Thanks for a great weekend , Francesca.

What a perfect little gem by the water. Francesca’s place is a great weekend getaway. Very friendly neighbors and host. Can’t beat the view from the cliff side! The coffee and breakfast foods provided were very generous and thoughtful. Thanks for everything!

Great stay! Enjoyed the location and property.

Cutest bungalow ever! Wonderful host who is available at all times. Beautiful sunsets seen from your own backyard. Great area to go exploring with lots of wonderful restaurants.

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.

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.

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!

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!

The house is just the right setting for a restful weekend near Chestertown. A short walk to town.

Very nice cottage in Chestertown! PJ was more than helpful! We look forward to our next trip!

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!

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!!

Cute and very stylish space in Rock Hall. We really enjoyed the peace and quiet - had a very relaxing weekend. Thank you.

We absolutely love Shipwright Cottage and we mean to make it our go-to whenever we visit my parents in Chestertown. It’s the most adorable little bungalow. The clever use of each nook and cranny is downright inspirational-I came home with a clear idea of what to do with my attic space :) Melissa was so accommodating and helpful, and the location is perfect. We are completely charmed. Thank you so much, Shipwright Cottage!

A very nice place to stay in Rock Hall. Thoughtful, well kept home. Well located. Quiet. Quick walk to water. Good value.

This cottage is a perfect getaway. It is sparkling clean and the decorating is stylish with cute personal touches. The owners were quick to respond to questions and were extremely accommodating. They left the lights on for our late Friday arrival and allowed us a late check out Sunday morning. They even have nice larger and soft bath towels. I would definitely stay here again.

What a wonderful place to stay ! Perfect for 4 people ! Would highly recommend and I would deff stay here again !

We were traveling on short notice for a funeral. Shipwright Cottage met all our lodging needs and then some! If you want a clean, modern & stylish “home away from home” just a short walk from the Bay - look no further! The back deck is a lovely place to relax and/or enjoy a meal. Our host went above & beyond to help ensure our stay was as seemless & enjoyable as possible. Thank you!

It was a beautiful house but a little less private that the pictures look. It is great for a couple weekend not for partying. People were great and loved the local florist. Even a restaurant/bar with great food less than a mile from the home.

This was the prefect house and location for the weekend. Quick responses and super clean

Beautiful place. It was our first Airbnb experience and it was more than I could have expected!! Loved it!!

Very clean, great amenities, and great location!!! Would recommend to anyone looking to spend time in Chestertown!!

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.

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!

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

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.

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.

Great location, amenities, communication, and check-in/out process. Perfect for our college reunion!

Great home in cute town. Would stay again.

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.

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!

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!!

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!

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!

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.

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.

Comfortable, with beautiful lighting fixtures!

A charming space with modern touches that's a short walk from all that Chestertown has to offer. We highly recommend it.

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.

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.

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.

Wonderful stay

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.

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.

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.

Beautifully decorated with great amenities. Perfect location to walk to town and college. Great space and Host was very responsive.

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.

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.

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!

We enjoyed our stay! Will definitely stay again.

Ryla was extremely accommodating and responsive. Loved staying at her place.

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.

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.

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.

Great service. Easy check in. 100% recommend

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!

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!

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!

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.

Convenient, comfortable, clean, and well equipped. Great hosts. Would stay there again.

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.

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.

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!

Great stay highly recommend Casa Carmen and The Retriever only blocks away.

Perfect accommodations to enjoy all Chestertown has to offer .

Walter was an excellent host, and his property was perfect. Thanks again for a great stay!

Wonderful place to stay! Highly recommend.

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.

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!

The perfect representation of cute Chestertown

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!!!

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.

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.

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!

This room is perfectly located walking distance from the University. Clean, quite and friendly.

Relaxing atmosphere and nice personal touches. Handy to have a small doemmsize fridge/freezer in the room. Hospitable hosts!

A beautiful house with incredible views. A stellar kitchen including a super fun built in brick pizza oven, and two dining areas suitable for large groups. A wonderful place for a few families to get together and enjoy the holiday!

House sits next to river so the view is very nice and relaxing. Great brick oven for pizzas. Communication with Jason was excellent and prompt.

Beautiful house with wonderful views! Loved the pizza oven! The place was very clean and well equipped for our weekend stay. The kids loved the ping pong in the basement. Overall we had a great stay! Hosts were very responsive before and during our stay. Highly recommend.

Beautiful home and special features through out! All pictures are exactly as the home is and more - in person and the views are just breath taking!! The home is huge and the brick oven, for our family, was a hit!! The fire pit on that chilly November evening, while watching the sun go down was a picture to remember. All and all it was a great birthday weekend and we loved it - great memories were made!

Perfect location for a family friendly getaway!

Perfect spot for a large family getaway. The location, kayaks, games, space and large tv were very appreciated. It was just really nice and comfortable with a great vibe.

Great House!!!

Beautiful and spacious home in a stunning and peaceful location.

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.

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.

Large space; great for a family gathering or big friend group. Loved the kitchen space and deck!!

Wonderful home in a beautiful area, everything was easy, accessible, and very clean upon arrival. Would definetly come back again.

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.

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.

Marcy & Ted have a nice place in Chestertown, it was clean and well decorated.

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.

Carey's house in Chestertown is a stylish home - it makes Chestertown an excellent experiennce.

Carey's home is beautiful and the location is great for walking to explore all places in downtown. I would highly recommend.

Third time staying here and it gets better and better. Location is perfect, and the house is like entering a museum.

Beautiful home and great location

A beautiful place to stay plenty of room and some. Meticulously clean .

Love this house! Fabulous kitchen. Beds were luxurious!

Carey is a wonderful host with a beautiful home. The location is perfect to town. Easy walk to the shops, restaurants and the river.

A great home, that focuses on the little things. Location is great for the Bay and a couple of real good restaurants / bars nearby.

Had a great stay at Jim’s place! Highly recommend.

This town is certainly a gem! But the accommodations made it so remarkable! Jim was more than helpful an accommodating & went above and beyond! This by far was one of THE BEST mini-vacations ever!

Jim and Dina were thoughtful hosts and the cottage was just as described. We very much enjoyed the space and had a wonderful weekend!

Very nice place, quiet and comfortable. Owners were awesome!

The bedroom and bathroom were immaculately clean and well appointed. The location was great and the hosts were very gracious. Highly recommend.

Sleek, streamlined room and bath appointed very efficiently and thoughtfully. Very comfy bed and adorable dog!

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!!

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.

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.

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!

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.

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.

Great place to stay! Rooms were in A++++ condition! Beautiful place. Gale and Jim were friendly and thoughtful!

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!

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.

A great place for a family getaway !

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.

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

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.

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.

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!

Cozy 3 bed room perfect for a family. Great location and easy to get to. Lots of parking and very speedy/professional responds.

The Pirates Perch was a great home. Spacious and loved the kitchen with the large island!! Home was provided with all that you need for your stay!! John was great to communicate with!! The home is located in the Heart of Rock Hall!! Close to all your needs such as food, beverages, shopping and fun!!! Wish we could have stayed longer!! Will recommend the home to our family and friends and we will stay here again without a doubt!!! Thanks again John!!!

We were visiting with 2 friends for a show right up the street at the Mainstay music club John’s house was beyond perfect. There are plenty of comfortable seating areas. We had a round of drinks and snacks before the show and made coffee that was provided the next morning before leaving. Plenty of room and we wished we could have stayed longer. John is excellent with communications.

Very quick to respond to any questions we had. The place was clean and close to some cute shops in the middle of town. Great trip overall!

Very hospitable. John was very helpful

Nice quiet cozy. Plenty of space for a family or small group. Good sized kitchen,2 baths, washer/dryer. Wish we were staying longer!

Love Johns place Would definitely recommend

John’s place was just right for us. Cozy old brick home in the heart of Rock Hall.

I booked the Blissful Retreat for my wife’s surprise birthday weekend. The cottage exceeded my high expectations in every way. Impeccably clean, beautifully decorated, private, serene, and quiet are just some of the attributes. Barbara also added so many little touches that made our weekend extra special. We will definitely return.

This is a nice cottage located about 7 minutes from Rock Hall where we were racing in the Watermen’s Olympic triathlon. Four of us stayed there two nights. This is an outbuilding/guest house located at the owner’s home but because of how it is situated, you have complete privacy. This is the first Airbnb that I’ve stayed at where the place is actually much bigger in person than the pictures make it look. We knew there wasn’t a full kitchen but we brought our grill and cooked dinner and enjoyed a nice meal at the dining room table on the first floor. There is a microwave and a toaster oven. There is plenty of glassware and dishes but a really tiny sink to wash them in. The bar area was nice to sit at each morning for coffee. We also enjoyed the front porch and had cocktails and listened to music while dinner grilled. The bedrooms are clean. The upstairs room is spacious. The downstairs bedroom is snug. There is only one bathroom and there is not a door except for the toilet. The shower is awesome with a steam setting. There were lots of helpful notes on how to use everything and they were very friendly notes not the fussy rules you find sometimes. There were lots of little touches like fresh half and half for our coffee and some muffins which were great for the race we were doing. Great little spot.

Clean, comfortable, lovely view!

I can not put into words how incredible this little slice of heaven is. Waking up to to see the sunrise right from bed was an amazing treat. The interior decorating was beautifully thought out and there are little hidden treasures everywhere you look. Extremely clean and lots of little extras. We were visiting for a wedding and my only regret is that we didn’t have more time to watch the willow sway in the wind from the porch and see the sunset on the water.

The Blissful Retreat is amazing, inside and out. The property is well-maintained and the house is spacious with loads of amenities. We brought a small tailgate grill to get around the lack of a full kitchen but could have easily gone into town for all our meals because it is so close. Our only regret is not being able to stay longer.

We loved staying at the Blissful Retreat/Cottage!! A relaxing, peaceful stay in a beautiful cottage with great amenities and thoughtful touches! Hope to come back again!

Everything was great. Barbara is a fantastic host. Absolutely recommend!

The name says it all! From the time we checked in until the time we checked out, we were happy and relaxed! The cottage was spotless and had great decor. It had all of the amenities we needed to relax and enjoy the weekend and Barbara was a great host! We have family in the area and I hope we will get to stay at The Blissful Retreat the next time we visit!

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!

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!

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.

Lovely house in such a cute little town. Highly recommend!

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.

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.

Thanks Phyllis and Pete for a wonderful stay in Chestertown! The house and location were perfect!

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!

Great old house and wonderful hospitality. Wonderful hosts.

Thomas's place was accurately described and our room was spacious. Thomas and his mom Nancy were very quick to respond to my messages and very welcoming and warm. Their place was exactly what we needed for our weekend retreat.

A great room in a great house very quiet and comfortable, and a lovely garden to enjoy outside

Thank you Thomas it was a wonderful stay looking forward to coming back soon...

Our room was impeccably clean, comfortable, beautiful! Thomas and his family were warm and inviting. This beautiful house is perfectly located to area attractions. Wonderful place to stay.

Very nice place in beautiful Maryland. We loved the interior design of our room, which made us feel at home the moment we arrived. Thomas was very nice, even though we arrived quite late! Thank you so much, would have liked to stay longer! Sven & Jan

Outstanding hospitality!

I loved how clean, and how comfortable the place was, 10/10

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!

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.

Very charming and clean space conveniently located to village of Chestertown. Host communicated very well, was warm, welcoming and friendly.

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

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.

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

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!

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!

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.

Charming home on a quiet street yet a convenient walk to town.

Great home!

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.

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.

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

This place is in an awesome location. Roland is an excellent host and is very quick to respond! We would definitely stay again.

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.

Bob and Diane are great hosts. Their house is very cozy and is in a great location in Rock Hall. We enjoyed our time and plan to come back again

Great place to stay in Rock Hall, MD. The hosts are great and you can tell they really care about their guests. House is very clean and in a nice quiet location. Plenty of parking and a overflow lot across the street. Will be back again in the future. Thanks for a great stay.

We had a wonderful stay at Bob and Diane’s place. It’s in a great, quiet location very close to downtown Rock Hall and it’s a lovely, peaceful place with a beautiful backyard garden. We could have sat watching the butterflies all day long! Bob and Diane were immediately responsive to all of our questions and the place was immaculately clean. We would definitely stay here again!

A very nice cottage with all the details and amenities needed for a great time in Rock Hall.....the bikes were a wonderful help!

We loved our stay at Bob's and Diane's cottage! We have 3 kids, and the cute and cozy cottage worked perfectly for us for a weekend getaway. There are 2 bedroom upstairs with 2 twin beds each. The master and the bathroom are downstairs. The back garden was just delightful, with its beautiful gardens, and sun lit reading room (potting shed:), and the front screened in porch was a nice too. The location was great- an easy walk or bike ride to town (we brought our own, but they had several loaners in the shed that they offered for our use). The owners were very quick to get back to us when we tripped a fuse and needed some help. And they were so kind as to leave us some welcome snacks upon our arrival! It was our first time to Rock Hall. The town is cute- very sleepy. We enjoyed the local beach during the day, as well as a private chartered boat ride (at Waterman's pier- the boat is called Island Girl, and his number is on the dock for you to call to make a reservation). We loved dining at both Passages and Waterman's. And the town's ice-cream shop ;)

Great little getaway. Lord riding bikes to town for coffee in the morning.

Great location. Very responsive hosts.

My friends and I had a wonderful time at Bob and Diane’s. Check-in and communication prior to our stay were smooth and uneventful and the house was spotless and exactly what we expected from the photos and listing. We loved having a glass of wine and hanging out on the screened-in porch and in the back garden. We were attending a wedding a few towns over so unfortunately didn’t get to spend much time in Rock Hall, but the town is only minutes away and looked super cute. Thanks for everything!