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Search results; 867 homes in Winchester

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Cabin in Winchester
VACATION CABIN - Sunday Morning Rentals
2 bedrooms, 2 beds, 1 private bathroom
20–25 Aug
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4.82 out of 5 average rating, 164 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, 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
4.97 out of 5 average rating, 66 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
15–20 Aug
4.95 out of 5 average rating, 86 reviews
Flat in Winchester
Beautifully Renovated Studio 2 miles from Marina!
1 queen bed, 1 bathroom
15–20 Aug
4.85 out of 5 average rating, 62 reviews
Top guest favourite
Home in Winchester
Latitude Adjustment - Lake Cottage
3 bedrooms, 6 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 110 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
1940 Renovated Cottage Near Square/Lake Summer Fun
2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
4.87 out of 5 average rating, 55 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
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, 88 reviews
Top guest favourite
Home in Tullahoma
Whiskey Trails Cottage
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.96 out of 5 average rating, 82 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
Guest favourite
Home in Winchester
Shady Cove Retreat With Peaceful Views & Firepit
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Winchester
LakeLane Landing Private dock Book now
2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cabin in Sewanee
Cabin 111 - the best in location and comfort!
1 bed, 1 bathroom
29 Aug – 3 Sept
4.95 out of 5 average rating, 325 reviews
Top guest favourite
Cottage in Pelham
The Milk Barn Cottage
2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 568 reviews
Top guest favourite
Cottage in Winchester
Tims Ford Lake! Modern Farmhouse
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
4.91 out of 5 average rating, 75 reviews
Home in Winchester
Peaceful 3BR Near Historic Downtown, Lake & Dining
3 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
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