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Search results; Over 1,000 homes in Winchester

Guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds, 1 private bathroom
21–26 Aug
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4.97 out of 5 average rating, 291 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
23–28 Aug
4.99 out of 5 average rating, 195 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed
28 Aug – 2 Sept
4.99 out of 5 average rating, 486 reviews
Top guest favourite
Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
1 queen bed
16–21 Aug
4.97 out of 5 average rating, 265 reviews
Top guest favourite
Room in Martinsburg
Wild & Wonderful -built in 1890
1 double bed
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
13–18 Aug
4.93 out of 5 average rating, 245 reviews
Top guest favourite
Guest house in New Market
Stay in a piece of history! Private Entire Cottage
2 beds
20–25 Sept
4.98 out of 5 average rating, 524 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
14–19 Sept
4.97 out of 5 average rating, 355 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom
15–20 Aug
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Guest suite in Clear Brook
Bluebird Bungalow
1 bedroom, 3 beds
20–25 Aug
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Cottage in Martinsburg
Last Rodeo Cottage
1 bedroom, 1 queen bed
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
9–14 Aug
4.91 out of 5 average rating, 275 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds
16–21 Aug
4.98 out of 5 average rating, 247 reviews
Top guest favourite
Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
2 beds
6–11 Sept
4.97 out of 5 average rating, 212 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 160 reviews
Top guest favourite
Farm stay in Warrenton
Winters Retreat Farm Cottage - Entire house
1 bedroom, 3 beds
23–28 Aug
4.97 out of 5 average rating, 750 reviews
Top guest favourite
Room in Shepherdstown
Little Big Sky! A cozy bedroom in the country!
1 queen bed
8–13 Aug
4.97 out of 5 average rating, 100 reviews
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
1 bedroom, 2 beds
30 Aug – 4 Sept
4.96 out of 5 average rating, 538 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds
9–14 Aug
4.98 out of 5 average rating, 122 reviews