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Search results; Over 1,000 homes in Winchester

Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds, 1.5 private bathrooms
10–15 Aug
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4.92 out of 5 average rating, 175 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 190 reviews, 1 queen bed, 1 bathroom
27 Jul – 1 Aug
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Flat in Winchester
Downtowner
4.97 out of 5 average rating, 353 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 481 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
4.93 out of 5 average rating, 243 reviews, 1 double bed, 1.5 bathrooms
21–26 Jul
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.9 out of 5 average rating, 273 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 245 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Aug
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
28 Jul – 2 Aug
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
5.0 out of 5 average rating, 88 reviews, 1 bedroom, 1.5 bathrooms
31 Jul – 5 Aug
Top guest favourite
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
4.95 out of 5 average rating, 125 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
4.95 out of 5 average rating, 39 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–24 Aug
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
4.98 out of 5 average rating, 221 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Home in Strasburg
"Shenandoah View"
4.96 out of 5 average rating, 24 reviews, 5 bedrooms, 6 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
4.97 out of 5 average rating, 119 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
21–26 Jul
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Guest suite in Winchester
Retro Vibe Studio
4.94 out of 5 average rating, 64 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Flat in Berkeley County
Private basement unit Bunker Hill, WV (WV-VA line)
5.0 out of 5 average rating, 22 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 159 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
5.0 out of 5 average rating, 27 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 55 reviews, 3 bedrooms, 5 beds, 2 bathrooms
24–29 Jul