
House vacation rentals in Dorchester County
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Top-rated house rentals in Dorchester County
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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
The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!

Peaceful Waterfront Home with Pool and Pier
The location looked exactly like the photos and the home was kept in great shape! The neighborhood was very quiet and peaceful with friendly neighbors! Overall, all amenities that were included with the stay were amazing. Mindy was also super responsive making our travel arrangements less stressful!

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!

"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

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.

Secluded River Front Cottage
Everything was great. Our family had a wonderful time at this spectacular location!

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!

Casa Maria heart of downtown.
I had a great stay! The place was clean, comfortable, and had everything I needed. I was in town for the Eagaman 70.3 Triathlon, and it was the perfect spot to relax before and after the race. Super easy check-in and a nice, quiet area. Would definitely stay here again.

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!

• 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!
Private house rentals

Tranquility on Talbot
Mary Beth was an amazing host. She made this vacation extremely stress free! The house was gorgeous, and the location is so peaceful! Mary made wonderful suggestions on places to eat and things to do! She was so accommodating and made this so easy! We will definitely be back to tranquility on talbot! ☺️

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.

Spacious Historic Craftsman only 3 blocks to water
This was great for our stay in town for the Ironman 70.3! Walkable to the race venue and a great neighborhood.

Farmhouse by the bay! Beach and pier access.
We had a lovely stay at Patrick’s place! It had everything we needed for a long weekend on the shore. A very comfortable home. Patrick was extremely responsive and helpful, with easy check in and check out. The kitchen was particularly lovely and well appointed! The house number is a little small so keep an eye out. And the mosquitos were fierce - don’t forget bug spray! Thanks, Patrick!

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!!

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!

Private Waterfront Retreat | Chesapeake Sunrise
We had a wonderful stay! The location was absolutely beautiful, and my family especially enjoyed having access to the private dock. We used the stand-up paddle boards, kayaks, and canoes every day after giving them a quick clean. The paddle boat didn’t work quite as expected, but we made it work with some oars and still had a great time on the water. The house itself was clean, comfortable, and well-stocked with everything we needed to prepare our own meals. The host also provided excellent local recommendations, which helped us make the most of our trip. Overall, it was a fantastic getaway, and I would definitely recommend this Airbnb to others!

Talbot Corner: Dog-Friendly 3-Bedroom Home
The home is beautiful and well kept. l really enjoyed my visit there.
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- Sandy Point State Park
- Quiet Waters Park
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Plantation Lakes Golf and Country Club
- Heritage Shores
- 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
- Piney Point Beach
- Lane Beach
- North Beach Boardwalk/Beach
- Lake Presidential Golf Club
- Triton Beach