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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
14–19 Aug
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4.93 out of 5 average rating, 310 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
13–18 Aug
4.99 out of 5 average rating, 193 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 484 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 354 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 275 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
13–18 Aug
4.93 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
3–8 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
3–8 Aug
4.98 out of 5 average rating, 222 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 247 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
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
12–17 Oct
4.94 out of 5 average rating, 66 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
4–9 Aug
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 160 reviews
Top guest favourite
Flat in Stephens City
Spacious Charming Basement Apt
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Berryville
The Cottage at Senseny
3 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
4.91 out of 5 average rating, 34 reviews
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds, 1 bathroom
30 Aug – 6 Sept
4.72 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 bedroom, 1 queen bed, 1 bathroom
7–12 Aug
4.99 out of 5 average rating, 260 reviews
Top guest favourite
Flat in Berkeley County
Private basement unit Bunker Hill, WV (WV-VA line)
1 bedroom, 1 bed, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 23 reviews