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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
7–12 Sept
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4.93 out of 5 average rating, 313 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 198 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Aug
4.98 out of 5 average rating, 248 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 489 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
18–23 Aug
4.93 out of 5 average rating, 248 reviews
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds, 1 bathroom
19–24 Aug
4.97 out of 5 average rating, 272 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
10–15 Oct
4.98 out of 5 average rating, 208 reviews
Top guest favourite
Guest house in New Market
Stay in a piece of history! Private Entire Cottage
2 beds, No bathroom
20–25 Sept
4.98 out of 5 average rating, 528 reviews
Top guest favourite
Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
1 bed, 1 bathroom
25–30 Aug
4.97 out of 5 average rating, 185 reviews
Top guest favourite
Boutique hotel in Capon Bridge
Sycamore Suite ~ 1 of 5 Unique Stays at Basswood
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.99 out of 5 average rating, 232 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
21–26 Aug
4.98 out of 5 average rating, 122 reviews
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 207 reviews
Guest favourite
Tiny home in Harpers Ferry
Romantic & Fun w/Amazing Overlook & Hot Tub
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 208 reviews
Guest favourite
Home in Winchester
Dog Friendly Mountain Retreat w/ Views & Firepit
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.86 out of 5 average rating, 49 reviews
Top guest favourite
Farm stay in Warrenton
Winters Retreat Farm Cottage - Entire house
1 bedroom, 3 beds, 1.5 bathrooms
25–30 Sept
4.97 out of 5 average rating, 755 reviews
Top guest favourite
Room in Fort Valley
Passage Creek Acres Room1
1 queen bed, WC
19–24 Aug
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Boutique hotel in Capon Bridge
Paw Paw Suite ~ 1 of 5 Unique Stays at Basswood
1 bedroom, 1 queen bed, 1 bathroom
19–24 Aug
4.99 out of 5 average rating, 268 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
18–23 Aug
4.95 out of 5 average rating, 40 reviews