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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 Jul
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4.99 out of 5 average rating, 477 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
6–11 Jul
4.99 out of 5 average rating, 188 reviews
Guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds, 1 bathroom
11–16 Aug
4.97 out of 5 average rating, 285 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 350 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Jul
4.9 out of 5 average rating, 269 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
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
2 bedrooms, 2 queen beds, 1.5 bathrooms
12–17 Jul
4.94 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
7–12 Jul
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 241 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
12–17 Jul
4.9 out of 5 average rating, 139 reviews
Guest favourite
Home in Winchester
Dog Friendly Mountain Retreat w/ Views & Firepit
3 bedrooms, 4 beds, 1 bathroom
8–13 Jul
4.86 out of 5 average rating, 49 reviews
Guest favourite
Home in Inwood
The Inwood House- easy on/off I-81
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Jul
4.95 out of 5 average rating, 554 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, 157 reviews
Superhost
Guest suite in Winchester
Cozy English Basement Apt
1 bedroom, 2 double beds, 1 bathroom
20–25 Jul
4.64 out of 5 average rating, 61 reviews
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 118 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed, 1.5 bathrooms
14–19 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
3 bedrooms, 3 beds, 1 bathroom
7–12 Aug
4.96 out of 5 average rating, 301 reviews
Top guest favourite
Cabin in Front Royal
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.97 out of 5 average rating, 71 reviews