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Search results; Over 1,000 homes in Winchester

Top guest favourite
Flat in Winchester
Old Town 1920s Gas Station with Hot Tub
1 bedroom, 1 bed, 1 private bathroom
10–15 Aug
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4.91 out of 5 average rating, 420 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
28 Aug – 2 Sept
4.99 out of 5 average rating, 485 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 355 reviews
Top guest favourite
Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
1 queen bed, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 265 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
Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
2 beds, 1 bathroom
6–11 Sept
4.97 out of 5 average rating, 212 reviews
Top guest favourite
Cabin in Rileyville
Ukiah Mountain Retreat
2 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 10 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
Cottage in Martinsburg
Last Rodeo Cottage
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 482 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
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Farm stay in Warrenton
Winters Retreat Farm Cottage - Entire house
1 bedroom, 3 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 749 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
9–14 Aug
4.98 out of 5 average rating, 121 reviews
Top guest favourite
Room in Martinsburg
Wild & Wonderful -built in 1890
1 double bed, 1 bathroom
6–11 Aug
5.0 out of 5 average rating, 48 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
Top guest favourite
Home in Martinsburg
So cozy
2 bedrooms, 2 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 92 reviews
Home in Strasburg
Strasburg Cottage Hideaway | Hot Tub + Sauna
2 bedrooms, 3 beds, 2 bathrooms
25–30 Aug
New place to stay
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
8–13 Aug
4.99 out of 5 average rating, 264 reviews