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Search results; Over 1,000 homes in Winchester

Guest favourite
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
1 bedroom, 3 beds, 1 bathroom
19–24 Jul
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4.74 out of 5 average rating, 725 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 477 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 188 reviews, 1 queen bed, 1 bathroom
6–11 Jul
Top guest favourite
Flat in Winchester
Downtowner
4.97 out of 5 average rating, 350 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 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
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.9 out of 5 average rating, 268 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 157 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
4.9 out of 5 average rating, 139 reviews, 3 bedrooms, 6 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
4.94 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 52 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 241 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
4.97 out of 5 average rating, 264 reviews, 1 bedroom, 2 beds, 1 bathroom
7–12 Jul
Superhost
Guest suite in Winchester
Cozy English Basement Apt
4.64 out of 5 average rating, 61 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Jul
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
14–19 Jul
Top guest favourite
Cabin in Luray
NEWCabin Retreat | Hot Tub, Fireplace & Fire Pit
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Home in Inwood
The Inwood House- easy on/off I-81
4.95 out of 5 average rating, 554 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
Guest favourite
Home in Winchester
Dog Friendly Mountain Retreat w/ Views & Firepit
4.86 out of 5 average rating, 49 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Jul
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
4.97 out of 5 average rating, 118 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
4.93 out of 5 average rating, 240 reviews, 1 double bed, 1.5 bathrooms
5–10 Jul