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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
7–12 Sept
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4.97 out of 5 average rating, 65 reviews
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Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 358 reviews
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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, 248 reviews
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Superhost
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.96 out of 5 average rating, 162 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
13–18 Sept
4.98 out of 5 average rating, 224 reviews
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Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 78 reviews
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Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 277 reviews
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Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
4.87 out of 5 average rating, 93 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
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
4.98 out of 5 average rating, 57 reviews
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Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
16–21 Sept
4.99 out of 5 average rating, 201 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
15–22 Sept
4.72 out of 5 average rating, 75 reviews
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Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 89 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
4.93 out of 5 average rating, 59 reviews
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Top guest favourite
Home in Strasburg
"Shenandoah View"
5 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 30 reviews
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Superhost
Room in Winchester
Private Room
1 single bed, 1 bathroom
14–19 Sept
4.82 out of 5 average rating, 11 reviews
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Superhost
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 491 reviews
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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, 42 reviews
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Top guest favourite
Home in Winchester
Bear Drop Inn, walking trails, pond, Winchester
4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 25 reviews