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
Home in South Pittsburg
5.0 out of 5 average rating, 26 reviewsCozy Cabin in the Clouds
May 3 – 10
Home in Winchester
4.93 out of 5 average rating, 30 reviewsRiver Retreat 4 bedrooms /4 bath w/ hot tub
Apr 4 – 11
Home in Hillsboro
5.0 out of 5 average rating, 17 reviewsFamily Friendly Country Home near The Caverns
May 13 – 20
Home in Gruetli-Laager
4.9 out of 5 average rating, 10 reviewsPool, Huge Backyard - Near Hiking & The Caverns
Aug 28 – Sep 4
Home in Winchester
5.0 out of 5 average rating, 6 reviewsNEW! Twin Creeks Marina Resort Oasis - 5 Stars
Nov 12 – 19
Home in Trenton
4.99 out of 5 average rating, 87 reviewsPool & Luxury Spa w/Mountain Views | Mins to Chatt
Jan 21 – 28
Home in Tracy City
4.92 out of 5 average rating, 38 reviewsLuxurious & Cozy Retreat Home on Mountain
Dec 18 – 25
Home in Trenton
4.84 out of 5 average rating, 76 reviewsSunset Haven: Pool with Stunning Views!
Aug 24 – 31
Quick stats about vacation rentals with a pool in Winchester
Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
770 reviews
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
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