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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
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
19–24 Jul
4.97 out of 5 average rating, 350 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds
1–6 Aug
4.98 out of 5 average rating, 241 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds
26–31 Jul
4.96 out of 5 average rating, 157 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
6–11 Jul
4.99 out of 5 average rating, 188 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds
12–17 Jul
4.9 out of 5 average rating, 139 reviews
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds
11–16 Jul
5.0 out of 5 average rating, 75 reviews
Guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds
11–16 Aug
4.97 out of 5 average rating, 285 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds
12–17 Jul
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds
12–17 Jul
4.9 out of 5 average rating, 269 reviews
Guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
2 bedrooms, 2 queen beds
12–17 Jul
4.94 out of 5 average rating, 50 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds
2–7 Aug
4.98 out of 5 average rating, 221 reviews
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds
11–16 Jul
4.91 out of 5 average rating, 47 reviews
Guest favourite
Home in Clear Brook
Sunrise/Sunset Views
4 bedrooms, 5 beds
19–24 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds
6–11 Jul
4.97 out of 5 average rating, 265 reviews
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds
6–11 Jul
4.92 out of 5 average rating, 174 reviews
Guest favourite
Flat in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 bedrooms, 2 beds
9–16 Aug
4.88 out of 5 average rating, 24 reviews
Top guest favourite
Cabin in Gerrardstown
Cozy Chalet Near Berkeley Springs & Harpers Ferry
2 bedrooms, 3 beds
3–8 Aug
4.98 out of 5 average rating, 200 reviews
Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds
28 Jul – 2 Aug
4.87 out of 5 average rating, 91 reviews