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Search results; Over 1,000 homes in Winchester

Top guest favourite
Flat in Winchester
Old Town 1920s Gas Station with Hot Tub
1 bedroom, 1 bed, 1 private bathroom
10–15 Aug
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4.91 out of 5 average rating, 420 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed
28 Aug – 2 Sept
4.99 out of 5 average rating, 487 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
23–28 Aug
4.99 out of 5 average rating, 195 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom
15–20 Aug
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
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
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
16–21 Aug
4.98 out of 5 average rating, 247 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds
16–21 Aug
4.98 out of 5 average rating, 223 reviews
Guest favourite
Home in Winchester
Modern Mountain House with Hot Tub & Views
3 bedrooms, 6 beds
9–14 Aug
4.9 out of 5 average rating, 10 reviews
Home in Strasburg
Strasburg Cottage Hideaway | Hot Tub + Sauna
2 bedrooms, 3 beds
25–30 Aug
New place to stay
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds
9–14 Aug
4.98 out of 5 average rating, 122 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed
3–8 Oct
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 160 reviews
Guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds
7–12 Aug
4.87 out of 5 average rating, 93 reviews
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds
9–14 Aug
4.9 out of 5 average rating, 145 reviews
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
1 bedroom, 3 beds
16–21 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Cabin in Luray
NEWCabin Retreat | Hot Tub, Fireplace & Fire Pit
2 bedrooms, 2 beds
22–27 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Martinsburg
Last Rodeo Cottage
1 bedroom, 1 queen bed
9–14 Aug
4.97 out of 5 average rating, 482 reviews
Top guest favourite
Home in Berryville
The Hill House at Stubblefield
2 bedrooms, 3 beds
6–11 Aug
4.98 out of 5 average rating, 80 reviews