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Search results; Over 1,000 homes in Winchester

Hotel in Winchester
Modern Hotel with Small Town Charm
1 bedroom, 1 bed, 1 private bath
Aug 14 – 19
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4.67 out of 5 average rating, 76 reviews
Top guest favorite
Cottage in Winchester
Hot tub with Blue Ridge Mountain views
4.99 out of 5 average rating, 487 reviews, 1 bedroom, 1 bed, 1 bath
Aug 28 – Sep 2
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Home in Winchester
Exposed brick, 2 blocks from downtown shops
5.0 out of 5 average rating, 88 reviews, 1 bedroom, 1.5 baths
Aug 15 – 20
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Home in Winchester
Renovated 1930s home near Old Town
4.98 out of 5 average rating, 223 reviews, 2 bedrooms, 2 beds, 2.5 baths
Aug 16 – 21
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Home in Winchester
Colonial home near Old Town Winchester
4.98 out of 5 average rating, 247 reviews, 3 bedrooms, 4 beds, 2.5 baths
Aug 16 – 21
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Apartment in Winchester
Mid-century design, one block from downtown
4.91 out of 5 average rating, 277 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 13 – 18
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Home in Winchester
Farmhouse on 106 acres near Winchester
4.96 out of 5 average rating, 161 reviews, 5 bedrooms, 6 beds, 1.5 baths
Aug 29 – Sep 3
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Home in Winchester
1800s stone home with private courtyard
5.0 out of 5 average rating, 78 reviews, 4 bedrooms, 4 beds, 3 baths
Aug 13 – 18
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Apartment in Winchester
1920s home near the pedestrian mall
4.97 out of 5 average rating, 356 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 14 – 19
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Home in Winchester
1731 farmhouse with a hot tub and sauna
4.87 out of 5 average rating, 93 reviews, 4 bedrooms, 5 beds, 2.5 baths
Aug 13 – 18
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Cottage in Berryville
18th-century cottage on a historic estate
4.98 out of 5 average rating, 122 reviews, 2 bedrooms, 2 beds, 1.5 baths
Aug 21 – 26
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Room in Winchester
5 minutes from historic downtown Winchester
4.99 out of 5 average rating, 197 reviews, 1 queen bed, 1 bath
Aug 23 – 28
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Cottage in Winchester
Stone cottage on 15 private acres
4.98 out of 5 average rating, 576 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 16 – 21
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Apartment in Winchester
Private entrance, 30 min from Shenandoah
5.0 out of 5 average rating, 77 reviews, 1 bedroom, 3 beds, 1 bath
Aug 16 – 21
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Home in Inwood
Renovated home with breakfast, 1 mile from I-81
4.95 out of 5 average rating, 566 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 3 – 8
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Home in Winchester
Historic gem with a basketball court
4.92 out of 5 average rating, 177 reviews, 3 bedrooms, 3 beds, 1.5 baths
Aug 13 – 18
Top guest favorite
Cottage in Martinsburg
Private cottage on 5 acres near DC
4.97 out of 5 average rating, 485 reviews, 1 bedroom, 1 bed, 1 bath
Aug 17 – 22
Top guest favorite
Apartment in Winchester
Renovated 1910 loft with exposed brick
4.99 out of 5 average rating, 262 reviews, 1 bedroom, 1 bed, 1 bath
Aug 13 – 18
Home in Strasburg
Hot tub, sauna, and fire pit
New place to stay, 2 bedrooms, 3 beds, 2 baths
Aug 25 – 30