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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 bed, 1 private bathroom
28 Aug – 2 Sept
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4.99 out of 5 average rating, 485 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 354 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
13–18 Aug
4.99 out of 5 average rating, 193 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 223 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 247 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 275 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
4–9 Aug
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 160 reviews
Home in Bolivar
Cozy Getaway Near History, Hiking & Adventure
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
New place to stay
Cabin in Bolivar
Black Bear Retreat • Modern Cabin in the Woods
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
9–14 Aug
4.98 out of 5 average rating, 121 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
4–9 Aug
4.95 out of 5 average rating, 40 reviews
Guest favourite
Home in Winchester
Dog Friendly Mountain Retreat w/ Views & Firepit
3 bedrooms, 4 beds, 1 bathroom
13–18 Aug
4.86 out of 5 average rating, 49 reviews
Top guest favourite
Home in Berryville
Deer Chase
3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
4.99 out of 5 average rating, 113 reviews
Guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 bathrooms
5–10 Aug
4.87 out of 5 average rating, 92 reviews
Top guest favourite
Home in Berryville
The Hill House at Stubblefield
2 bedrooms, 3 beds, 2.5 bathrooms
4–9 Aug
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds, 3 bathrooms
6–11 Aug
5.0 out of 5 average rating, 78 reviews
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
4.98 out of 5 average rating, 57 reviews