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Search results; Over 1,000 homes in Winchester

Top guest favourite
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 bedroom, 1 bed, 1 private bathroom
16–21 Aug
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4.99 out of 5 average rating, 262 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed
13–18 Sept
4.99 out of 5 average rating, 488 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds
17–22 Aug
4.98 out of 5 average rating, 248 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom
22–27 Aug
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
2 bedrooms, 3 beds
17–22 Aug
4.95 out of 5 average rating, 106 reviews
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds
6–11 Sept
4.95 out of 5 average rating, 207 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds
25–30 Aug
4.98 out of 5 average rating, 223 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
23–28 Aug
4.99 out of 5 average rating, 198 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, 161 reviews
Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds
17–22 Aug
4.87 out of 5 average rating, 93 reviews
Guest favourite
Cabin in Front Royal
Cozy Retreat near Shenandoah River HotTub•Wineries
3 bedrooms, 3 queen beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds
17–22 Aug
4.97 out of 5 average rating, 272 reviews
Guest favourite
Home in Winchester
Dog Friendly Mountain Retreat w/ Views & Firepit
3 bedrooms, 4 beds
16–21 Aug
4.86 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
14–19 Sept
4.97 out of 5 average rating, 357 reviews
Home in Strasburg
Strasburg Cottage Hideaway | Hot Tub + Sauna
2 bedrooms, 3 beds
25–30 Aug
New place to stay
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
1 bedroom, 1 king bed
24–29 Aug
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Augusta
Hart's Overlook | Hot Tub, Stunning Mtn Views+Pond
1 bedroom, 1 king bed
7–12 Sept
4.92 out of 5 average rating, 166 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds
10–15 Oct
4.98 out of 5 average rating, 208 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds
21–26 Aug
4.98 out of 5 average rating, 122 reviews