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Search results; Over 1,000 homes in Winchester

Photo 1 of 29
Top guest favourite
Cottage in Winchester
Avery Pines Cottage
1 bedroom, 1 bed, 1 private bathroom
21–26 Sept
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4.97 out of 5 average rating, 69 reviews
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Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.97 out of 5 average rating, 359 reviews
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Townhouse in Winchester
Brewhouse renovated row house steps from downtown
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 109 reviews
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Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 164 reviews
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Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Nov
4.98 out of 5 average rating, 249 reviews
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Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 224 reviews
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Home in Winchester
The Cozy Brick Cottage on Opequon Ave
3 bedrooms, 3 beds, 1.5 bathrooms
20–25 Oct
4.67 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 58 reviews
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Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds, 3 bathrooms
19–24 Oct
4.94 out of 5 average rating, 64 reviews
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Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 45 reviews
Photo 1 of 29
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Oct
4.9 out of 5 average rating, 280 reviews
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Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 147 reviews
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Superhost
Room in Winchester
Private Room
1 single bed, 1 bathroom
1–6 Oct
4.85 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Clear Brook
Sunrise/Sunset Views
4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 13 reviews
Photo 1 of 29
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 93 reviews
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Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
12–17 Oct
4.99 out of 5 average rating, 496 reviews
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Top guest favourite
Home in Winchester
Misty Meadow has quite setting in the country.
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Oct
4.93 out of 5 average rating, 91 reviews
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Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds, 3 bathrooms
13–18 Nov
5.0 out of 5 average rating, 80 reviews
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Top guest favourite
Home in Martinsburg
Charming Home Explore, Relax, and Enjoy
4 bedrooms, 4 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 23 reviews