
Vacation rentals with a pool in Winchester
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winchester
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 Winchester rentals with a pool
House rentals with a pool

Twin Creeks Getaway, Pet Friendly!

Lake House in Winchester, Tn w/Golf Cart

Quail Run Farm House, 15 Mins to Chattanooga

Lakefront, Boats Included, 3 Fireplaces, Gorgeous!

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

Pool, Huge Backyard - Near Hiking & The Caverns

Forest Retreat: Poolside Bliss Close to Campus

Lake House Dreams
Other vacation rentals with a pool

The Acorn at 12 Oaks Vacation Rental.

NEW! Twin Creeks Marina Resort Oasis - 5 Stars

Spacious Family Gem: Golf Cart - 2 Ensuites - Pool

Private Hot Tub & Pool & backroad to caverns

Serenity by the lake...your home away from home!

Raccoon Mountain Rustic Cabin in Campground

Private indoor pool & sauna

Architect-Designed Luxury Treehouse near Sewanee
Quick stats about vacation rentals with a pool in Winchester
Total rentals
40 properties
Nightly prices starting at
$190 CAD before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
40 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Destinations to explore
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- Tennessee Aquarium
- Cloudland Canyon State Park
- Monte Sano State Park
- Sweetens Cove Golf Club
- Black Creek Club
- Chattanooga Golf and Country Club
- Coolidge Park
- Chattanooga Choo Choo
- The Ledges
- The Lookout Mountain Club
- Old Fort Golf Course
- Creative Discovery Museum
- Hunter Museum of American Art
- National Medal of Honor Heritage Center
- Kyujo-mae Station