
House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Dorchester County house rentals
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!

Turtle's Nest - Hist. Cambridge
David and Wendy’s home was the perfect place for our family participating in and supporting the Cambridge Ironman with an easy walk to the course and to the Main Street. They went above and beyond accommodating our requests, since we were traveling with a two month old and a two year old. We were very comfortable and loved our evenings in the screened in porch and pool. We would love to stay at David and Wendy’s again.

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!

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!

"Goose Landing" Waterfront Retreat
It is NOT possible to find something negative to say about this property. Absolutely wonderful! Hubby and I went for a week to celebrate his retirement and Father’s Day. I really just wanted some peace and quiet from the chaos of the renovation influencers who recently moved in next to our home. Lol. This property has PEACE in spades! You’ll feel like the only people on earth. Yet nice restaurants and shopping are just down the road. The setting is beautiful. We spent much of our time on the screened in porch watching the abundant wildlife. We swam, canoed, explored and just relaxed. The house itself is amazing. So comfortable with tons of seating for everyone. The gorgeous kitchen has everything you’d need, and there’s an appliance closet filled with goodies. You have TWO Keurigs, Doug! Lol. Super comfy beds, awesome showers. You will not be disappointed. We hated leaving and will be back! Doug is super responsive, and couldn’t be nicer. You will not regret choosing this home ❤️
Weekly house rentals

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.

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!

Stunning Views, Remodeled Family-Friendly Home
This was a truly lovely and clean home. Staying there was so wonderful - sitting on the screened porch listening to the water, walking the waterfront, lovely. It was so peaceful and calming of a location. Also, walking or biking distance to the St. Marys college and historical park. I recommend anyone stay there - I would again. We felt so comfortable and welcomed into this gorgeous waterfront property. You cannot beat the views and location. Communicative hosts. Thanks for a great stay!

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!

• 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!

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse
Our stay was wonderful. The house was clean, had beautiful views from the bedrooms, and was the perfect place to relax. The kitchen was fully stocked (e.g. ketchup, mustard, coffee pods), and a lot of appliances. The air fryer came in very handy. The outdoor space was truly amazing. The screened porch was great for reading, evening meals, and relaxing. Being on the bay meant lots of water fun on kayaks and paddle boards. Our hosts were very thoughtful in the way they prepared the house for guests. Anytime we had a question, they were very quick to respond. I would highly recommend this place to anyone who enjoys nature and quiet peacefulness.

Blackwater Refuge Lodge
Glen's place was a perfect retreat for our large group. Access to the water for kayaks and paddle boards, close enough to the small town of Cambridge to easily get there, great wildlife refuge within minutes with great walking and bike trails. Couldn't beat the location. We already want to make plans to come back if they will have us. We encountered a small problem when we checked in, but Julia and Glen addressed it immediately and went out of their way to provide a solution for our group. Julia was a great host and always responsive. We would definitely stay here again. Highly recommended!

SoMD Waffle House 1.5 acres of cozy coastal living
We really enjoyed our stay here. It was relaxing and super chill.
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!

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
Me encantó muy cómodo bonita la playa y organizado se los recomiendo

Waterfront with sweeping bay view & private beach
We had such a wonderful trip to the Bay! What a beautiful spot! Such lovely views of the bay- with sights of sailboats, ships, rays, and even dolphins one day! It felt very private and quiet: exactly what a vacation should feel like! We loved using the kayaks and searching for shells/shark teeth! The home itself was extremely clean and comfortable to be in. Full kitchen was super helpful when feeding a whole family! It was our first solo trip with small kids and was honestly wonderful in every sense! Colin was very easy and pleasant to communicate with. 10/10- would recommend to anyone!

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

Charming Summer Cottage – Relax and Unwind Here!
This was the perfect place to stay for a few days of peace and tranquility! The house was beautiful and everything was fresh and clean! The host was incredibly helpful and responsive. Everything was as described in the listing. We loved the quiet of the neighborhood and took a lot of walks. Highly recommend staying here if you are considering a visit to this area!!

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).

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!
Destinations to explore
- Rentals with breakfast Dorchester County
- Kid-friendly rentals Dorchester County
- Pet-friendly rentals Dorchester County
- Rentals with a fireplace Dorchester County
- Rentals with outdoor seating Dorchester County
- Apartment rentals Dorchester County
- Rentals with a fire pit Dorchester County
- Rentals with a patio Dorchester County
- Rentals with a washer and dryer Dorchester County
- Beachfront rentals Dorchester County
- Rentals with lake access Dorchester County
- Rentals with pools Dorchester County
- Rentals with a hot tub Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
- Rentals with a kayak 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
- Maryland Renaissance Festival
- Quiet Waters Park
- Plantation Lakes Golf and Country Club
- Heritage Shores
- Six Flags America
- Flounder Pavilion Beach Front - Sandy Point State Park
- Ragged Point Beach
- Gerry Boyle Park
- Breezy Point Beach & Campground
- Sandyland Beach
- Chesapeake Beach Water Park
- Rose Haven Memorial Park
- Idlewilde Restoration Project
- Matapeake Clubhouse and Beach
- Saint Jerome Beach
- Piney Point Beach
- Oxford Beach
- Bayfront Beach
- Brownies Beach
- Quiet Waters Dog Beach
- Severn Beach
- Guard Shore
- Langford Sand