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Search results; Over 1,000 homes in Winchester

Guest favourite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
1 bedroom, 2 beds, 1.5 private bathrooms
13–18 Aug
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4.93 out of 5 average rating, 309 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 190 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 353 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 481 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Jul
4.9 out of 5 average rating, 273 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
21–26 Jul
4.93 out of 5 average rating, 243 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Aug
4.98 out of 5 average rating, 245 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed, 1.5 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 125 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 221 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
17–24 Aug
4.95 out of 5 average rating, 39 reviews
Guest suite in Winchester
Cozy English Basement Apt
1 bedroom, 2 double beds, 1 bathroom
22–27 Jul
4.64 out of 5 average rating, 61 reviews
Top guest favourite
Home in Strasburg
"Shenandoah View"
5 bedrooms, 6 beds, 2.5 bathrooms
2–7 Aug
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
4.96 out of 5 average rating, 159 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
26–31 Jul
4.94 out of 5 average rating, 64 reviews
Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
4.98 out of 5 average rating, 571 reviews
Top guest favourite
Flat in Berkeley County
Private basement unit Bunker Hill, WV (WV-VA line)
1 bedroom, 1 bed, 1 bathroom
21–26 Jul
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
26–31 Jul
4.97 out of 5 average rating, 119 reviews