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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
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 190 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 353 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Jul
4.9 out of 5 average rating, 273 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Aug
4.98 out of 5 average rating, 245 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 221 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
26–31 Jul
4.9 out of 5 average rating, 142 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
4.96 out of 5 average rating, 159 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
24–29 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
4.98 out of 5 average rating, 571 reviews
Guest favourite
Home in Millwood
Peony Place renovated farmhouse in horse country
2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 203 reviews
Guest favourite
Home in Winchester
Modern Mountain House with Hot Tub & Views
3 bedrooms, 6 beds, 2 bathrooms
28 Jul – 2 Aug
4.88 out of 5 average rating, 8 reviews
Home in Basye
Pet friendly treehouse at Bryce & Lake Laura
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
New place to stay
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Front Royal
Shenandoah Twilight | Hot Tub + Sunset Views
2 bedrooms, 2 beds, 1 bathroom
7–12 Aug
4.96 out of 5 average rating, 161 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
17–24 Aug
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds, 3 bathrooms
15–20 Aug
4.92 out of 5 average rating, 49 reviews
Guest suite in Winchester
Cozy English Basement Apt
1 bedroom, 2 double beds, 1 bathroom
21–26 Jul
4.64 out of 5 average rating, 61 reviews