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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
26–31 Jul
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4.99 out of 5 average rating, 481 reviews
Top guest favourite
Flat in Winchester
Downtowner
4.97 out of 5 average rating, 353 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 191 reviews, 1 queen bed, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 246 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Aug
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.9 out of 5 average rating, 273 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 159 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
4.98 out of 5 average rating, 221 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Aug
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
4.9 out of 5 average rating, 142 reviews, 3 bedrooms, 6 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 55 reviews, 3 bedrooms, 5 beds, 2 bathrooms
24–29 Jul
Guest favourite
Home in Winchester
Modern Mountain House with Hot Tub & Views
4.88 out of 5 average rating, 8 reviews, 3 bedrooms, 6 beds, 2 bathrooms
28 Jul – 2 Aug
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 2 beds, 1 bathroom
26–31 Jul
Superhost
Cabin in Front Royal
Whispering Tides River Cabin | *Skyline, Vineyards
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
4.92 out of 5 average rating, 49 reviews, 3 bedrooms, 3 beds, 3 bathrooms
15–20 Aug
Top guest favourite
Cabin in High View
Mary's Cabin
4.98 out of 5 average rating, 204 reviews, 1 bedroom, 4 beds, 1 bathroom
25–30 Oct
Guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
4.88 out of 5 average rating, 24 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
4.98 out of 5 average rating, 571 reviews, 2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Guest favourite
Home in Millwood
Peony Place renovated farmhouse in horse country
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
4.95 out of 5 average rating, 39 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–24 Aug
Guest suite in Winchester
Cozy English Basement Apt
4.64 out of 5 average rating, 61 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Jul