
House holiday rentals in Dorchester County
Find and book unique houses on Airbnb
Top-rated house rentals in Dorchester County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Dorchester County
House rentals with a pool

Family Retreat - Private Pool, 4 Bedroom, Fire Pit
Where do I start? My boyfriend and I randomly chose Ann’s place for a quick weekend getaway knowing nothing about the town or Bivalve. It was such a great trip! Very quiet little town with the nicest locals! Ann and Eddie came by and took us in the golf cart and sharing a little about the town. Ann’s space was PERFECT and CLEAN! So peaceful and relaxing. Having the pool was great for the few hot days we had. Absolutely loved and recommend visiting this quaint little town and staying at Ann’s if you get the chance!

Waterfront Paradise with a Private Pool
Such an amazing place! Joanne was super responsive and flexible. The views were unmatched! Perfect Mommy and Daddy getaway and we will certainly be back with the kids!

Spacious and private waterfront, sleeps 10
The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!

Peaceful Waterfront Home with Pool and Pier
Our favorite Airbnb stay! Every aspect of this house was well executed & thoughtful. Fantastic layout of the house allowed our family to be as connected as we wanted yet had private places to retreat. The pool was perfect and the dock had everything you could ask for with fishing and crabbing. The kitchen was stocked with anything you would possibly need. Very quiet and calm location, yet near to grocery and restaurants. We couldn’t have asked for a better vacation spot. Mindy was awesome and available for any questions that we had. We are so grateful for this great family vacation spot!

Relax by the Water - Summer Dates Available!
Four old friends enjoyed a long weekend at this beautiful home. The water views were spectacular and the many amenities (pool, hot tub, outdoor relaxing seating) made us never want to leave. We stayed home most of the time electing only to venture out for dinner Saturday night. All that said it is quite remote so may not be suitable for all vacationers.

Bay Front Villa on Chesapeake
Great host who was very responsive. Very nice house, clean, with beautiful views. Lots of space and things to do on sight. Perfect for a peacful private get away

Serenity Bay-Priv Pool-ask about 2-night stays!
A really great place! Beautiful, peaceful surroundings. House was perfect for a family getaway. Kitchen was well stocked. Room layout allowed for togetherness and privacy. The fire pit was super nice and the lake was great for the kids. Highly recommend!
Weekly house rentals

Aurora Blue - A stylish experience
Aurora Blue is stunning, no detail was left out of the planning. The space is well planned to allow privacy and quiet when resting. Each room has a en suite bathroom and the master suite is beyond 5 star. The home was immaculate, having coffee and paper products available was an extra bonus. Great patio for sitting outside and quiet at night without any disturbances. We locked ourselves out and the host came onsite quickly to address the problem we created. Excited to go back one day.

Beachfront Oasis with Amazing Views
We had such a wonderful stay! The kitchen was incredibly well stocked—honestly better than my own at home—with 5-6 large pots, an Instant Pot, every spice you could think of,peelers (which saved me!), and both a NutriBullet and a regular blender. It made cooking for the family a breeze. The kid had a blast on the trampoline, and we all loved the easy beach access with calm waters perfect for swimming all day and kayaking. The beach was also perfect for a peaceful morning run, and at night we could see the lighthouse light on the water. The porch quickly became our favorite spot—we gathered there to watch a rainstorm and were treated to a stunning double rainbow. The sky was full of stars at night, creating such a peaceful atmosphere. The grill on the porch made cooking super convenient. We enjoyed being close to a large park where we played pickleball. The beds were large and comfortable—everyone slept really well. Michael was a fantastic host—very attentive and accommodating.

Waterfront with sweeping bay view & private beach
We recently stayed at Colin’s Airbnb in Lusby, MD, and it was an absolute gem. Nestled right by the ocean, the home was quaint, peaceful, and filled with charm. The views and the serenity of the surroundings made our getaway feel truly special. Colin was a wonderful host—quick to respond, kind, and genuinely pleasant to chat with. When we reached out for local bakery recommendations for our daughter’s birthday cake, he gladly shared a few. We ended up choosing one and couldn’t have been happier—the cake was perfect! The home itself was cozy and comfortable. The IKEA bedding added a clean, modern touch and made for a restful night’s sleep. There was just the right amount of space for the three of us to relax and enjoy our time together. Thank you, Colin, for making our stay memorable—we’d love to return someday!

You'll enjoy the The Great Escape in Cambridge!
Clare was super responsive, and got right back to me with recommendations for restaurants and answering any questions. The home was great for our party and we were able to walk downtown to restaurants and shops. Beds and pillows were very comfortable. Overall a great stay!

Hambrooks House - Porched Sanctuary near Choptank
Loved my stay beautiful home with serene surroundings and lots of local historic attractions. Highly recommend James’ place!

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse
One of the best places we have stayed! Nice and peaceful! We had the best time at Maria’s place.

• Peaceful Point • A relaxing waterfront retreat
Peaceful point was stunningly beautiful! A perfect place for adults and kids to unwind and enjoy the scenic views and beautiful nature. Joanna was the best host and surprised us with a little welcome package with a kind welcome card and some of our favorite treats from Trader Joe’s! She was so helpful and responsive via text. Can’t thank her enough!

Stunning Chesapeake waterfront home
We had a truly wonderful stay at this beautiful home! The place was spotless and very well maintained, and we felt comfortable from the moment we arrived. There were plenty of activities to enjoy as a family, and we created some unforgettable memories here. The host was incredibly friendly and responded quickly to any questions we had, which made everything even more enjoyable. The surroundings are absolutely stunning, and the sunset views were nothing short of magical. We would love to come back again!
Private house rentals

Water views, w/BBQ, patio, near downtown& beach!
Perfect for our group for the weekend. Owners are very responsive and accommodating! Cozy and well kept house. Would book again!

ChesapeakeWaterfront - HotTub_FirePit_Kayak_Arcade
We had a wonderful stay! The house was absolutely charming—beautifully decorated, clean, and perfectly situated on a peaceful lake. It offered the best of both worlds: a quiet, relaxing retreat while still being just a short drive from town if we needed anything. Julie was an exceptional host—kind, helpful, and incredibly responsive. We truly couldn’t have asked for a better experience. I highly recommend both the home and Julie as a host—you won’t be disappointed!

Waterfront, amazing views, pier, fishing/crabbing
The house are clean, bright with a great view. We had a wonderful time and were lucky to have wonderful weather during our stay! We also had a lot of fun playing Mad Gab and other games in the games chest. We were successful in catching some fish and plenty of crabs. It was a great vacation. We enjoyed it very much.

Beachfront Chesapeake Bay Retreat
I loved it, very comfortable, nice beach and organized, I recommend it

Riverview Retreat
This served as a low key weekend retreat for us. We unplugged and enjoyed being in each other’s company. Being on the river, surrounded by trees and birdwatching was exactly what we needed. The kitchen was well appointed so we were able to enjoy family favorite activities (cooking together and playing board games).

Bay Front Beach House
We booked this place for a weekend getaway with our little ones. It was absolutely the perfect place for what we were planning! The private beach was PERfECT for young children! the kids loved being able to ride their scooters under the house. We got some fishing in, daughter was a spot master! The hammock was lost in a storm before we arrived, but our superhost made sure we could enjoy a hammock!! upon hearing that it was the top of the list of kids wish list, she took time out of her day and drove all the way and installed a new hammock for us!! Was even so considerate to offer to pick up any needed items. I believe more than the kids, my dog had the time of his life!! They even had doggy bowls ready!! We will definitely be back!! This place is awesome!! Thank you Dana for you gracious hospitality!!

Scenic Bay Hideaway: Peaceful Vibes & Beach Access
Tricia was incredible and her place is beautiful, clean and fun! She has provided lots of additional, thoughtful and couldn't have been nicer. Highly Recommend for anyone who is looking for a peaceful, beach getaway!

Private beach with comfort
We were able to check in earlier which was great tho some of us weren’t able to get there right away… we enjoyed our stay very peaceful and were wishing we could have one more day! 😊 we were going to grill burgers but couldn’t find grill utensils so just did our best inside and still turned out great!!! Thank you for your house and allowing us to stay there!
Destinations to explore
- Rentals with a washing machine and dryer Dorchester County
- Rentals with a kayak Dorchester County
- Rentals with pools Dorchester County
- Rentals with outdoor seating Dorchester County
- Flat rentals Dorchester County
- Pet-friendly rentals Dorchester County
- Family-friendly rentals Dorchester County
- Rentals with a hot tub Dorchester County
- Rentals with a firepit Dorchester County
- Rentals with a fireplace Dorchester County
- Rentals with lake access Dorchester County
- Beachfront rentals Dorchester County
- Rentals with breakfast Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
- Rentals with a patio Dorchester County
- House rentals Maryland
- House rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Sandy Point State Park
- Quiet Waters Park
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Heritage Shores
- Plantation Lakes Golf and Country Club
- Gerry Boyle Park
- Ragged Point Beach
- Six Flags America
- Breezy Point Beach & Campground
- Chesapeake Beach Water Park
- Idlewilde Restoration Project
- Sandyland Beach
- Bayfront Beach
- Brownies Beach
- Rose Haven Memorial Park
- Quiet Waters Dog Beach
- Oxford Beach
- Matapeake Clubhouse and Beach
- Lake Presidential Golf Club
- Guard Shore
- Langford Sand
- Lane Beach
- Piney Point Beach