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Search results; Over 1,000 homes in Winchester

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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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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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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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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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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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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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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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Religious building in Stephens City
The Sanctuary in the Shenandoah Valley
3 bedrooms, 6 beds, 2 bathrooms
1–6 Sept
4.96 out of 5 average rating, 136 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
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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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
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Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 208 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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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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Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 123 reviews
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Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
1–6 Sept
4.93 out of 5 average rating, 249 reviews
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Home in Inwood
Farm-Lane Retreat w/ Game Room • 1 Min to I-81
3 bedrooms, 6 beds, 3 bathrooms
13–18 Oct
5.0 out of 5 average rating, 35 reviews
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Superhost
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
4.98 out of 5 average rating, 57 reviews