
Vacation rentals with a pool in Dorchester County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Dorchester County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Dorchester County rentals with a pool
House rentals with a pool
Top guest favorite

Home in Cambridge
5 out of 5 average rating, 13 reviewsWaterfront Oasis-SaltwaterPool/HotTub/FirePit/Dock
Top guest favorite

Home in Bivalve
4.96 out of 5 average rating, 28 reviewsFamily Retreat - Private Pool, 4 Bedroom, Fire Pit
Superhost

Home in Ridge
4.87 out of 5 average rating, 61 reviewsWaterfront Paradise with a Private Pool

Home in Cambridge
4.78 out of 5 average rating, 9 reviewsOutrigger at Swan Cove Manor

Home in Cambridge
4.71 out of 5 average rating, 17 reviewsCrabby Casa; Choptank waterfront w/ pool and dock!
Top guest favorite

Home in Lusby
5 out of 5 average rating, 12 reviewsBliss By The Bay Chalet
Guest favorite

Home in Cambridge
4.86 out of 5 average rating, 14 reviewsWaterfront Cambridge Home: Pool & Dock!
Superhost

Home in Tilghman Island
4.94 out of 5 average rating, 36 reviewsTranquility on Tilghman Island – Wide Water Views
Other vacation rentals with a pool

Home in Trappe
4.73 out of 5 average rating, 15 reviewsSpacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Townhouse in Cambridge
New place to stay< 1 Mi to Dtwn: Waterfront Townhome in Cambridge!

Home in Deal Island Historic District
1 Mi to Boat Ramp: Peaceful Deal Island Home!
Guest favorite

Townhouse in Cambridge
4.9 out of 5 average rating, 10 reviewsWalk to Dtwn: Waterfront Eastern Shore Townhome!
Destinations to explore
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- Rentals with pools Maryland
- Rentals with pools United States
- Sandy Point State Park
- Six Flags America
- Breezy Point Beach & Campground
- Piney Point Beach
- Plantation Lakes Golf and Country Club
- Ragged Point Beach
- Quiet Waters Park
- Chesapeake Beach Water Park
- Sandyland Beach
- Heritage Shores
- Rose Haven Memorial Park
- Gerry Boyle Park
- Flounder Pavilion Beach Front - Sandy Point State Park
- North Beach Boardwalk/Beach
- Bayfront Beach
- St George Island Beach
- Franklin Manor Community Private Park
- Guard Shore
- Idlewilde Restoration Project
- Matapeake Clubhouse and Beach
- Lake Presidential Golf Club
- Brownies Beach
- Oxford Beach
- Triton Beach