
Holiday rentals with a pool in Talbot County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Talbot County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Talbot County rentals with a pool
House rentals with a pool

Waterfront Escape with Pool Nature Lover Paradise

Eastern Shore Family Getaway

Waterfront, Pool, Dock, Hot Tub.Stunning Views! A

Private Pool, Bay Views near Kentmorr Bar & Beach

River Lure estate - Waterfront, Pool, Hot Tub

Waterfront Private Dock & Pool Near Cambridge

Grace Creek Cottage

Waterfront Bliss: Ultimate Tilghman Retreat
Other holiday rentals with a pool

Luxury Waterfront St. Michaels Home

Family & Friends Paradise – Pool, BBQ, & More!

On the Choptank River

The Point at Little Choptank

Pet-Friendly Stay with Pool – Relax & Unwind!

Relax by the Water - Summer Dates Available!

10 Minutes to St. Michaels with a Private Pool

Luxury Oasis, Pool, Hot Tub & Walk to Beach
Destinations to explore
- Rentals with lake access Talbot County
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- Rentals with a fireplace Talbot County
- Pet-friendly rentals Talbot County
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- Beachfront rentals Talbot County
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- Rentals with a hot tub Talbot County
- Kid-friendly rentals Talbot County
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- Nationals Park
- The White House
- National Mall
- Betterton Beach
- District Wharf
- Oriole Park at Camden Yards
- Smithsonian National Museum of Natural History
- National Museum of African American History and Culture
- M&T Bank Stadium
- Hampden
- Sandy Point State Park
- Patterson Park
- Washington Monument
- Big Stone Beach
- National Harbor
- Six Flags America
- Maryland Renaissance Festival
- Crystal Beach Manor, Earleville, MD
- National Air and Space Museum
- Smithsonian American Art Museum
- Lincoln Park
- Library of Congress
- Killens Pond State Park
- Plantation Lakes Golf and Country Club