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Search results; Over 1,000 homes in Winchester

Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 private bathroom
19–24 Jul
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4.97 out of 5 average rating, 350 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 188 reviews, 1 queen bed, 1 bathroom
17–22 Jul
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 Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 478 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 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
21–26 Aug
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
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.9 out of 5 average rating, 270 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 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
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
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
5.0 out of 5 average rating, 75 reviews, 1 bedroom, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Cabin in High View
Mary's Cabin
4.97 out of 5 average rating, 199 reviews, 1 bedroom, 4 beds, 1 bathroom
20–25 Sept
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
5.0 out of 5 average rating, 26 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 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
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
Room in Winchester
We Welcome You to Winchester! Best reviews!
4.93 out of 5 average rating, 241 reviews, 1 double bed, 1.5 bathrooms
13–18 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, 51 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
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
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
4.95 out of 5 average rating, 39 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Jul
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