Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester
Guest favourite
Guest house in Tullahoma
4.99 out of 5 average rating, 81 reviewsWoodland Ct. Cottage
13–20 Jul
€ 139 per night
Guest favourite
Home in Winchester
4.97 out of 5 average rating, 34 reviewsBasecamp Retreat TimsFordLake
24 Feb – 3 Mar
€ 266 per night
Guest favourite
Tiny home in Tullahoma
5.0 out of 5 average rating, 18 reviewsWhiskey Woods Retreat-Hot Tub
24–31 Oct
€ 126 per night
Guest favourite
Farm stay in Shelbyville
4.98 out of 5 average rating, 65 reviewsCircle C Alpaca Farm - Entire apartment
24 Sep – 1 Oct
€ 110 per night
Guest favourite
Holiday home in Winchester
4.93 out of 5 average rating, 14 reviewsLakeside Laurel | Community Pool & Lake Access
20–27 Aug
€ 243 per night
Guest favourite
Cabin in Winchester
5.0 out of 5 average rating, 17 reviewsThe Cabins At Rivers Edge
28 Jun – 5 Jul
€ 207 per night
Guest favourite
Home in Decherd
5.0 out of 5 average rating, 59 reviewsNear The Caverns and Sewanee w/ Tesla / EV charger
7–14 Jan
€ 197 per night
Guest favourite
Home in Winchester
5.0 out of 5 average rating, 19 reviewsPeaceful Lakehouse Perfect for a Getaway at TFL
20–27 Oct
€ 278 per night
Quick stats about holiday rentals in Winchester
Total rentals
120 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
2.4K reviews
Nightly prices starting at
€ 19 before taxes and fees
Destinations to explore
- Chattanooga Holiday rentals
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- Pet-friendly rentals Winchester
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