Holiday houses 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
Guesthouse in Tullahoma
4.99 out of 5 average rating, 80 reviewsWoodland Ct. Cottage
8–15 Jan
$242 NZD per night
Guest favourite
Home in Winchester
4.97 out of 5 average rating, 34 reviewsBasecamp Retreat TimsFordLake
28 Apr – 5 May
$447 NZD per night
Guest favourite
Holiday home in Winchester
4.92 out of 5 average rating, 13 reviewsLakeside Laurel | Community Pool & Lake Access
17–24 Jun
$437 NZD per night
Guest favourite
Farm stay in Shelbyville
4.98 out of 5 average rating, 61 reviewsCircle C Alpaca Farm - Entire apartment
27 Sep – 4 Oct
$196 NZD per night
Guest favourite
Home in Decherd
5.0 out of 5 average rating, 59 reviewsNear The Caverns and Sewanee w/ Tesla / EV charger
16–23 Feb
$354 NZD per night
Guest favourite
Tiny home in Estillfork
5.0 out of 5 average rating, 61 reviewsBeautiful Mountain View over looking creek!!
10–17 Jan
$186 NZD per night
Guest favourite
Home in Winchester
5.0 out of 5 average rating, 17 reviewsPeaceful Lakehouse Perfect for a Getaway at TFL
6–13 Aug
$503 NZD per night
Guest favourite
Tiny home in Tullahoma
5.0 out of 5 average rating, 17 reviewsWhiskey Woods Retreat-Hot Tub
26 May – 2 Jun
$280 NZD 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
$34 NZD before taxes and fees
Destinations to explore
- Chattanooga Holiday rentals
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- Franklin Holiday rentals
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- Guntersville Holiday rentals
- Murfreesboro Holiday rentals
- Rising Fawn Holiday rentals
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- Rentals with outdoor seating Winchester
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- Rentals with a washing machine and dryer Winchester
- Rentals with lake access Winchester
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