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Search results; 855 homes in Winchester

Guest favourite
Home in Winchester
Hydrotherapy Haven
3 bedrooms, 5 beds, 3 private bathrooms
2–7 Oct
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5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Winchester
The Hangout on Heath Lane
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 68 reviews
Home in Winchester
Cozy Tims Ford lakehouse with private dock
3 bedrooms, 3 beds, 2 bathrooms
19–24 Aug
New place to stay
Guest favourite
Home in Winchester
The Bourbon Embassy at Twin Creeks
4 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Winchester
Lakeside Retreat Marina/Pool, Golf Cart, Game Room
4 bedrooms, 6 beds, 3.5 bathrooms
31 Aug – 5 Sept
4.97 out of 5 average rating, 66 reviews
Guest favourite
Flat in Winchester
Winchester's Premier Downtown Loft! Near The Lake!
2 bedrooms, 2 king beds, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 90 reviews
Guest favourite
Tiny home in Winchester
Tiny House
1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
4.95 out of 5 average rating, 86 reviews
Guest favourite
Flat in Winchester
Unbeatable Charm & Convenience On The Square!
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 72 reviews
Flat in Winchester
Beautifully Renovated Studio 2 miles from Marina!
1 queen bed, 1 bathroom
23–28 Aug
4.86 out of 5 average rating, 63 reviews
Top guest favourite
Cabin in Tullahoma
Cozy Cabin close to Tims Ford Lake & Jack Daniels
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Aug
4.94 out of 5 average rating, 218 reviews
Top guest favourite
Townhouse in Winchester
Lovin Lake Life
5 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 48 reviews
Guest favourite
Home in Winchester
Shady Cove Retreat With Peaceful Views & Firepit
3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Cottage in Pelham
The Milk Barn Cottage
2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 568 reviews
Top guest favourite
Home in Winchester
Meadow View Retreat
2 bedrooms, 2 queen beds, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 85 reviews
Guest favourite
Home in Winchester
*Rare Find* Flat lot, Best Views, Dock Waterslide
4 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 11 reviews
Home in Winchester
The Yellow Cottage by Tims Ford Lake
3 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.68 out of 5 average rating, 111 reviews
Guest favourite
Home in Tullahoma
Whiskey Trails Cottage
2 bedrooms, 3 beds, 1 bathroom
5–10 Sept
4.96 out of 5 average rating, 82 reviews
Guest favourite
Home in Winchester
Dry Jack Tim-Hot Tub, Water Views, Marina
4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Aug
4.84 out of 5 average rating, 31 reviews
Guest favourite
Home in Estill Springs
Dragonfly Cove
5 bedrooms, 6 beds, 2.5 bathrooms
19–24 Aug
5.0 out of 5 average rating, 8 reviews