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Search results; Over 1,000 homes in Winchester

Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds, 1.5 private bathrooms
10–15 Aug
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4.92 out of 5 average rating, 175 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
2–7 Aug
4.97 out of 5 average rating, 352 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, 158 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
19–24 Jul
4.99 out of 5 average rating, 189 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, 245 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds
14–19 Jul
4.98 out of 5 average rating, 55 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds
19–24 Jul
4.9 out of 5 average rating, 140 reviews
Top guest favourite
Home in Clear Brook
Sunrise/Sunset Views
4 bedrooms, 5 beds
21–26 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 bedrooms, 2 beds
21–28 Jul
4.88 out of 5 average rating, 25 reviews
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds
26–31 Jul
5.0 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds
19–24 Jul
4.9 out of 5 average rating, 271 reviews
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
2 bedrooms, 2 queen beds
9–14 Aug
4.94 out of 5 average rating, 53 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed
15–20 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
26–31 Jul
4.94 out of 5 average rating, 63 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
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds
8–13 Sept
4.91 out of 5 average rating, 47 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
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed
26–31 Jul
4.99 out of 5 average rating, 479 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds
14–19 Jul
4.95 out of 5 average rating, 39 reviews