
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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Dorchester County rentals with a pool
House rentals with a pool

Family Retreat - Private Pool, 4 Bedroom, Fire Pit

Waterfront Paradise with a Private Pool

Beach House | An ESVR Property

Peaceful Waterfront Home with Pool and Pier

Bliss By The Bay Chalet

The Point at Little Choptank

Waterfront Cambridge Home: Pool & Dock!

Fall at Combsberry – Private Waterfront Estate
Other vacation rentals with a pool

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Walkable Condo w/ Drawbridge Views in Cambridge

1 Mi to Boat Ramp: Peaceful Deal Island Home!

Farm House Stay on the Eastern Shore of Maryland

Warwick Farms waterfront Retreat

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge!

Walk to Dtwn: Waterfront Eastern Shore Townhome!

Waterfront Paradise | Pool, Views & Serenity
Destinations to explore
- Cottage rentals Dorchester County
- Rentals with a hot tub Dorchester County
- Rentals with a fire pit Dorchester County
- Rentals with breakfast Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
- Rentals with a fireplace Dorchester County
- Apartment rentals Dorchester County
- Rentals with outdoor seating Dorchester County
- Family-friendly rentals Dorchester County
- Rentals with a washer and dryer Dorchester County
- Pet-friendly rentals Dorchester County
- Beachfront rentals Dorchester County
- Rentals with lake access Dorchester County
- Rentals with a kayak Dorchester County
- House rentals Dorchester County
- 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
- Quiet Waters Park
- Ragged Point Beach
- Chesapeake Beach Water Park
- Heritage Shores
- Gerry Boyle Park
- Sandyland Beach
- Rose Haven Memorial Park
- Flounder Pavilion Beach Front - Sandy Point State Park
- Bayfront Beach
- North Beach Boardwalk/Beach
- St George Island Beach
- Franklin Manor Community Private Park
- Guard Shore
- Idlewilde Restoration Project
- Matapeake Clubhouse and Beach
- Brownies Beach
- Lake Presidential Golf Club
- Oxford Beach
- Triton Beach