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Search results; 837 homes in Winchester

Guest favourite
Home in Winchester
Dock on Lake! Walk to Downtown Shops/Rest/Movies!
3 bedrooms, 5 beds, 2 shared bathrooms
7–12 Sept
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4.9 out of 5 average rating, 132 reviews
Top guest favourite
Home in Winchester
The Hangout on Heath Lane
2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 66 reviews
Top guest favourite
Home in Winchester
Lakeside Retreat Marina/Pool, Golf Cart, Game Room
4 bedrooms, 6 beds, 3.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 65 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, 87 reviews
Guest favourite
Home in Winchester
The Bourbon Embassy at Twin Creeks
4 bedrooms, 6 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Tiny home in Winchester
Tiny House
1 bedroom, 1 bed, 1 bathroom
10–15 Aug
4.95 out of 5 average rating, 86 reviews
Guest favourite
Home in Winchester
Luxury 3BR lakeside escape
3 bedrooms, 1 sofa bed, 3 bathrooms
10–15 Aug
4.88 out of 5 average rating, 41 reviews
Guest favourite
Room in Estill Springs
Draft Horse Barn Bedroom.
2 beds, 1 bathroom
24–29 Aug
4.92 out of 5 average rating, 137 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, 71 reviews
Top guest favourite
Home in Estill Springs
Waterfront Access | Lake Views | Dock | Pool Table
3 bedrooms, 7 beds, 3 bathrooms
2–8 Nov
4.99 out of 5 average rating, 110 reviews
Flat in Winchester
Beautifully Renovated Studio 2 miles from Marina!
1 queen bed, 1 bathroom
14–19 Aug
4.85 out of 5 average rating, 62 reviews
Home in Winchester
Peaceful 3BR Near Historic Downtown, Lake & Dining
3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
New place to stay
Top guest favourite
Home in Winchester
Waterfront Oasis On Tims Ford Lake: Pool/Kayak!
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
4.98 out of 5 average rating, 81 reviews
Home in Estill Springs
Lakefront Retreat with private 2-Story Dock
4 bedrooms, 7 beds, 2 bathrooms
12–17 Aug
New place to stay
Top guest favourite
Cottage in Pelham
The Milk Barn Cottage
2 beds, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 568 reviews
Guest favourite
Home in Tullahoma
Whiskey Trails Cottage
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.98 out of 5 average rating, 80 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
Top guest favourite
Home in Winchester
Cozy Lake Cottage W/Pool, Hot Tub,Kayaks, SUPs
3 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 91 reviews
Top guest favourite
Home in Winchester
Barefoot Retreat w/kayaks/SUP/Game Room/Pool
3 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
4.99 out of 5 average rating, 69 reviews