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Search results; Over 1,000 homes in Winchester

Top guest favourite
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 bedroom, 1 bed, 1 private bathroom
13–18 Aug
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4.99 out of 5 average rating, 262 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
23–28 Aug
4.99 out of 5 average rating, 197 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, 487 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 Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
1 bed
15–20 Aug
4.97 out of 5 average rating, 184 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, 248 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds
13–18 Aug
4.91 out of 5 average rating, 277 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
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds
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
20–25 Sept
4.98 out of 5 average rating, 525 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
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
Boutique hotel in Capon Bridge
Sycamore Suite ~ 1 of 5 Unique Stays at Basswood
1 bedroom, 2 beds
25–30 Aug
4.99 out of 5 average rating, 231 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
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
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
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bedroom, 1 bed
16–21 Aug
4.95 out of 5 average rating, 125 reviews
Top guest favourite
Boutique hotel in Capon Bridge
Paw Paw Suite ~ 1 of 5 Unique Stays at Basswood
1 bedroom, 1 queen bed
19–24 Aug
4.99 out of 5 average rating, 267 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