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Search results; Over 1,000 homes in Winchester

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Top guest favourite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
2 bedrooms, 3 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.95 out of 5 average rating, 109 reviews
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Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 359 reviews
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Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 164 reviews
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Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 224 reviews
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Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom
20–25 Sept
5.0 out of 5 average rating, 93 reviews
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Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 249 reviews
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Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed
12–17 Oct
4.99 out of 5 average rating, 496 reviews
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Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds
20–25 Sept
4.94 out of 5 average rating, 64 reviews
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Home in Winchester
The Cozy Brick Cottage on Opequon Ave
3 bedrooms, 3 beds
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
19–24 Sept
4.98 out of 5 average rating, 58 reviews
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Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds
18–23 Oct
4.95 out of 5 average rating, 211 reviews
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Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds
19–24 Sept
4.98 out of 5 average rating, 127 reviews
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Guest favourite
Flat in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 bedrooms, 2 beds
26 Oct – 2 Nov
4.88 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Clear Brook
Sunrise/Sunset Views
4 bedrooms, 5 beds
4–9 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
30 Sept – 5 Oct
4.99 out of 5 average rating, 206 reviews
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Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds
19–24 Sept
4.95 out of 5 average rating, 44 reviews
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Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds
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
23–28 Sept
4.85 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds
30 Oct – 4 Nov
4.87 out of 5 average rating, 93 reviews