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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 bed, 1 private bathroom
28 Aug – 2 Sept
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4.99 out of 5 average rating, 485 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
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
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
5–10 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
4–9 Aug
4.95 out of 5 average rating, 40 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
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
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
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
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 Clear Brook
Bluebird Bungalow
1 bedroom, 3 beds, 1 bathroom
4–9 Aug
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 223 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
Old Town Loft In Highly Desirable Area Downtown
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 261 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
Top guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
4.92 out of 5 average rating, 176 reviews
Top guest favourite
Flat in Berkeley County
Private basement unit Bunker Hill, WV (WV-VA line)
1 bedroom, 1 bed, 1 bathroom
4–9 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds, 3 bathrooms
6–11 Aug
5.0 out of 5 average rating, 78 reviews