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Search results; Over 1,000 homes in Winchester

Guest favourite
Cottage in Winchester
Secluded Mountain Top Retreat | Stunning Views
1 bedroom, 2 beds, 1 private bathroom
5–10 Jul
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4.88 out of 5 average rating, 40 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
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
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
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds, 1 bathroom
6–11 Jul
4.97 out of 5 average rating, 264 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
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
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
13–18 Jul
4.99 out of 5 average rating, 477 reviews
Top guest favourite
Cabin in Gerrardstown
Cozy Chalet Near Berkeley Springs & Harpers Ferry
2 bedrooms, 3 beds, 1.5 bathrooms
3–8 Aug
4.98 out of 5 average rating, 200 reviews
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
1 bedroom, 1 king bed, 1 bathroom
25–30 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
13–18 Jul
4.93 out of 5 average rating, 241 reviews
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds, 1 bathroom
15–22 Aug
4.72 out of 5 average rating, 75 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
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bedroom, 1 bed, 1 bathroom
7–12 Aug
4.95 out of 5 average rating, 125 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, 50 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
5–10 Jul
4.94 out of 5 average rating, 62 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
Bear Drop Inn, walking trails, pond, Winchester
4 bedrooms, 7 beds, 3.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 24 reviews