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Search results; 856 homes in Winchester

Guest favourite
Cabin in Winchester
Private Dock - Best Cabin Tims Ford Lake
2 bedrooms, 4 beds, 1 private bathroom
16–21 Aug
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4.86 out of 5 average rating, 211 reviews
Top guest favourite
Home in Winchester
The Hangout on Heath Lane
2 bedrooms, 3 beds
12–17 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
16–21 Aug
4.97 out of 5 average rating, 66 reviews
Guest favourite
Home in Winchester
The Bourbon Embassy at Twin Creeks
4 bedrooms, 6 beds
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Tiny home in Winchester
Tiny House
1 bedroom, 1 bed
12–17 Aug
4.95 out of 5 average rating, 86 reviews
Guest favourite
Flat in Winchester
Winchester's Premier Downtown Loft! Near The Lake!
2 bedrooms, 2 king beds
23–28 Aug
4.89 out of 5 average rating, 88 reviews
Flat in Winchester
Beautifully Renovated Studio 2 miles from Marina!
1 queen bed
14–19 Aug
4.85 out of 5 average rating, 62 reviews
Top guest favourite
Home in Estill Springs
Waterfront Access | Lake Views | Dock | Pool Table
3 bedrooms, 7 beds
2–8 Nov
4.99 out of 5 average rating, 110 reviews
Guest favourite
Flat in Winchester
Unbeatable Charm & Convenience On The Square!
2 bedrooms, 3 beds
23–28 Aug
4.89 out of 5 average rating, 71 reviews
Top guest favourite
Home in Winchester
Latitude Adjustment - Lake Cottage
3 bedrooms, 6 beds
13–18 Aug
4.96 out of 5 average rating, 109 reviews
Guest favourite
Home in Winchester
Luxury 3BR lakeside escape
3 bedrooms, 1 sofa bed
24–29 Aug
4.88 out of 5 average rating, 41 reviews
Guest favourite
Home in Tullahoma
Whiskey Trails Cottage
2 bedrooms, 3 beds
22–27 Aug
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Home in Winchester
Dock, Water Views, Kayaks, Fire Pit, Game Room
3 bedrooms, 7 beds
16–21 Aug
5.0 out of 5 average rating, 81 reviews
Guest favourite
Home in Winchester
By the pool
4 bedrooms, 6 beds
16–21 Aug
4.82 out of 5 average rating, 11 reviews
Home in Estill Springs
Lakefront Retreat with private 2-Story Dock
4 bedrooms, 7 beds
14–19 Aug
New place to stay
Top guest favourite
Townhouse in Winchester
Lovin Lake Life
5 bedrooms, 7 beds
23–28 Aug
5.0 out of 5 average rating, 48 reviews
Guest favourite
Home in Winchester
Lake Retreat w/Marina, Golf Cart, Game Room, Pool
4 bedrooms, 8 beds
13–18 Aug
4.99 out of 5 average rating, 84 reviews
Superhost
Treehouse in Monteagle
Scandinavian Treetop Bliss @ Terralodge
1 bedroom, 2 beds
13–18 Aug
4.85 out of 5 average rating, 694 reviews
Guest favourite
Home in Winchester
LakeLane Landing Private dock Book now
2 bedrooms, 3 beds
22–27 Aug
5.0 out of 5 average rating, 7 reviews