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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, 487 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
23–28 Aug
4.99 out of 5 average rating, 196 reviews
Top guest favourite
Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
1 bed
14–19 Aug
4.97 out of 5 average rating, 184 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds
12–17 Aug
4.91 out of 5 average rating, 277 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
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed
12–17 Aug
4.93 out of 5 average rating, 248 reviews
Top guest favourite
Room in Fort Valley
Passage Creek Acres Room1-Cottage
1 queen bed
16–21 Aug
5.0 out of 5 average rating, 28 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
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, 525 reviews
Top guest favourite
Room in Shepherdstown
Little Big Sky! A cozy bedroom in the country!
1 queen bed
16–21 Aug
4.97 out of 5 average rating, 101 reviews
Top guest favourite
Farm stay in Warrenton
Winters Retreat Farm Cottage - Entire house
1 bedroom, 3 beds
3–8 Oct
4.97 out of 5 average rating, 753 reviews
Top guest favourite
Cottage in Martinsburg
Last Rodeo Cottage
1 bedroom, 1 queen bed
17–22 Aug
4.97 out of 5 average rating, 485 reviews
Top guest favourite
Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
1 queen bed
27 Sept – 2 Oct
4.97 out of 5 average rating, 267 reviews
Top guest favourite
Home in Martinsburg
So cozy
2 bedrooms, 2 beds
22–27 Aug
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Flat in The Plains
Rose End
1 bedroom, 1 queen bed
20–25 Aug
4.98 out of 5 average rating, 717 reviews
Guest favourite
Tiny home in Harpers Ferry
Romantic & Fun w/Amazing Overlook & Hot Tub
1 bedroom, 2 beds
14–19 Sept
4.96 out of 5 average rating, 208 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, 161 reviews
Top guest favourite
Cabin in Rileyville
Ukiah Mountain Retreat
2 bedrooms, 5 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Farm stay in Edinburg
Circle F Ranch Bunkhouse- Elevated Farm Stay
2 bedrooms, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 20 reviews