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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
13–18 Sept
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4.99 out of 5 average rating, 488 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
15–20 Aug
5.0 out of 5 average rating, 88 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, 248 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 198 reviews
Top guest favourite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
2 bedrooms, 3 beds, 2 bathrooms
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, 1 bathroom
15–20 Aug
4.95 out of 5 average rating, 206 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
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
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, 2.5 bathrooms
16–21 Aug
4.87 out of 5 average rating, 93 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 356 reviews
Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 154 reviews
Guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
3 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
4.89 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
10–15 Oct
4.98 out of 5 average rating, 208 reviews
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds, 3 bathrooms
6–11 Sept
4.93 out of 5 average rating, 55 reviews
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.97 out of 5 average rating, 271 reviews
Top guest favourite
Cabin in Great Cacapon
Modern Mountain Cabin w/hot tub!
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
21–26 Aug
4.98 out of 5 average rating, 122 reviews
Home in Strasburg
Strasburg Cottage Hideaway | Hot Tub + Sauna
2 bedrooms, 3 beds, 2 bathrooms
25–30 Aug
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