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Search results; Over 1,000 homes in Winchester

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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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Top guest favourite
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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Home in Winchester
The Cozy Brick Cottage on Opequon Ave
3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Sept
4.67 out of 5 average rating, 3 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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Top guest favourite
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
Photo 1 of 29
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 249 reviews
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Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
4.98 out of 5 average rating, 58 reviews
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Superhost
Room in Winchester
Private Room
1 single bed, 1 bathroom
23–28 Sept
4.85 out of 5 average rating, 13 reviews
Photo 1 of 29
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
19–24 Sept
4.95 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds, 3 bathrooms
20–25 Sept
4.94 out of 5 average rating, 64 reviews
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Home in Winchester
Misty Meadow has quite setting in the country.
2 bedrooms, 2 beds, 1.5 bathrooms
5–10 Oct
4.93 out of 5 average rating, 91 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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Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 496 reviews
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Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds, 1 bathroom
19–26 Oct
4.72 out of 5 average rating, 76 reviews
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Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 93 reviews
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Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Sept
4.98 out of 5 average rating, 127 reviews
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Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 276 reviews
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Top guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed, 1.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 19 reviews