
Holiday rentals in Dorchester County
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Top-rated holiday rentals in Dorchester County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Dorchester County
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Cottage in Westover
4.87 out of 5 average rating, 69 reviewsMartha’s Cottage•at Old Beauchamp Homestead•
KendraRating, 5 stars5 months ago
It was a peaceful and quiet weekend getaway. The house was cozy and perfect for our trip. We can’t wait to come back and visit again.
Top guest favourite

Townhouse in Cambridge
5 out of 5 average rating, 28 reviewsCheerful 3-Bedroom Townhouse Steps from the Resort
KristiRating, 5 stars6 months ago
This townhouse was fabulous in every way—Darryl has everything you need for a lovely stay, and the house was bright, clean, and comfortable. The location close to the resort is a plus for those who want to take advantage of its amenities. I definitely would stay here again!
Guest favourite

Cottage in Lusby
4.9 out of 5 average rating, 31 reviewsElk Cottage-Lake Lariat / Private lake access
ShellyRating, 5 stars1 month ago
Britta's home was perfect for all of us! The kitchen had everything we needed and more. The home is spacious and in a quiet area with a beautiful view of the lake. The beds were super comfortable and everything was so clean! we look forward to staying again in the future! thank you Britta!
Guest favourite

Home in Scotland
4.91 out of 5 average rating, 128 reviewsSpacious Gorgeous Waterfront Home with Sunset View
RonRating, 5 stars1 month ago
This house is perfect for large groups. It is very spacious, with plenty of room to spread out and get comfortable. We enjoyed sitting on the dock taking in the serene natural beauty of the Creek and observing the local birdlife, including Kingfishers, Great Blue Herons, and Bald Eagles. The house is situated very near to the entrance of Lookout Point State Park which we greatly enjoyed exploring on bicycles. Seeing a large wedge of Tundra Swans fly overhead was a special moment. If you want to spend some time relaxing in a beautiful setting in a beautiful and very interesting area with a large group, this house will serve you well.
Top guest favourite

Home in Cambridge
4.98 out of 5 average rating, 45 reviewsWaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse
AlanRating, 5 stars1 week ago
Everything was exactly as advertised, plus many extra touches that made our stay great. Would like to come back when the temp is a little warmer, but the hot tub and water access were perfect even for early spring. Thanks Maria!
Guest favourite

Home in Lusby
4.92 out of 5 average rating, 13 reviewsRiverview Retreat
JonRating, 5 stars3 months ago
The house was perfect for our family get-away. There is enough room for everyone and yet the large public space made it easy to congregate. The kitchen is amazing for the cooking a meal and there was a great selection of movies when we came back tired and wanted to unwind. It was quite cold out but the house was warm and cosy and we enjoyed our time hanging out there.
Top guest favourite

Home in Taylors Island
4.97 out of 5 average rating, 39 reviewsA Vacation for All, Away From It All
ChristyneRating, 5 stars4 months ago
If you are looking for a peaceful escape, you found it. Although this home can be used for large gatherings, it is also the perfect getaway for 2. My husband and I loved watching the water and the natural wildlife. DO NOT MISS THE OPPORTUNITY TO EXPERIENCE THIS HOUSE!
Top guest favourite

Home in Cambridge
5 out of 5 average rating, 15 reviewsEastern Shore Getaway
StephanieRating, 5 stars6 months ago
My family and I had a wonderful stay at Erika’s place! She was incredibly accommodating and flexible with our check-in time, making the whole process smooth. The house itself was beautiful, spacious, and perfect for spreading out. It’s also very kid-friendly—Erika thoughtfully provided plenty of toys and coloring books, which made the stay even more enjoyable for the little ones.
Destinations to explore
- Beachfront rentals Dorchester County
- Rentals with a hot tub Dorchester County
- Rentals with a washing machine and dryer Dorchester County
- Rentals with a patio Dorchester County
- Family-friendly rentals Dorchester County
- Flat rentals Dorchester County
- Rentals with outdoor seating Dorchester County
- Rentals with a firepit Dorchester County
- House rentals Dorchester County
- Rentals with pools Dorchester County
- Rentals with lake access Dorchester County
- Rentals with a fireplace Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
- Rentals with a kayak Dorchester County
- Pet-friendly rentals Dorchester County
- Rentals with breakfast Dorchester County
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- Sandy Point State Park
- Heritage Shores
- Six Flags America
- Gerry Boyle Park
- Quiet Waters Park
- Maryland Renaissance Festival
- Ragged Point Beach
- Langford Sand
- Plantation Lakes Golf and Country Club
- Idlewilde Restoration Project
- Quiet Waters Dog Beach
- Matapeake Clubhouse and Beach
- Sparrows Beach
- Guard Shore
- Lane Beach
- Saint Jerome Beach
- Brownies Beach
- Oxford Beach
- Chesapeake Beach Water Park
- Rose Haven Memorial Park
- Triton Beach
- Lake Presidential Golf Club
- Carrs Beach
- Flounder Pavilion Beach Front - Sandy Point State Park