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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
19–24 Jul
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4.99 out of 5 average rating, 478 reviews
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
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 188 reviews, 1 queen bed, 1 bathroom
10–15 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
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
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
Guest favourite
Home in Clear Brook
Sunrise/Sunset Views
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
5.0 out of 5 average rating, 75 reviews, 4 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
4.91 out of 5 average rating, 47 reviews, 3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.9 out of 5 average rating, 269 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Winchester
City Charmer minutes from Old Town
4.97 out of 5 average rating, 285 reviews, 2 bedrooms, 2 beds, 1 bathroom
11–16 Aug
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
4.94 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
4.94 out of 5 average rating, 63 reviews, 1 bed, 1 bathroom
16–21 Jul
Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4.87 out of 5 average rating, 91 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
28 Jul – 2 Aug
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
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
4.92 out of 5 average rating, 175 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
4.97 out of 5 average rating, 265 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
4.98 out of 5 average rating, 116 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul