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Search results; Over 1,000 homes in Winchester

Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds, 1 private bathroom
28 Jul – 2 Aug
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4.97 out of 5 average rating, 266 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
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 188 reviews
Guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds, 1 bathroom
21–26 Aug
4.97 out of 5 average rating, 285 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 479 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 270 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, 140 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, 244 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, 54 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
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, 51 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, 242 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 200 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
4.96 out of 5 average rating, 158 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
13–18 Jul
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
16–21 Jul
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 88 reviews
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
4.92 out of 5 average rating, 175 reviews
Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
2 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
4.98 out of 5 average rating, 568 reviews