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Search results; Over 1,000 homes in Winchester

Guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds, 1 private bathroom
21–26 Aug
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4.97 out of 5 average rating, 291 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
28 Aug – 2 Sept
4.99 out of 5 average rating, 485 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
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 88 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
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 355 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
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
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
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
Home in Strasburg
Strasburg Cottage Hideaway | Hot Tub + Sauna
2 bedrooms, 3 beds, 2 bathrooms
25–30 Aug
New place to stay
Guest favourite
Home in Winchester
Modern Mountain House with Hot Tub & Views
3 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 bathrooms
6–11 Aug
4.87 out of 5 average rating, 93 reviews
Guest favourite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
3 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
4.95 out of 5 average rating, 310 reviews
Cabin in Bolivar
Black Bear Retreat • Modern Cabin in the Woods
2 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
New place to stay
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
Top guest favourite
Home in Martinsburg
Architectural Mountaintop Retreat | Shenandoah
4 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.98 out of 5 average rating, 575 reviews
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
9–14 Aug
4.9 out of 5 average rating, 145 reviews