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Search results; Over 1,000 homes in Winchester

Flat in Winchester
Nostalgia Lane 3 BR in the heart of the city
3 bedrooms, 3 beds, 1 private bathroom
12–17 Aug
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4.85 out of 5 average rating, 240 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, 195 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, 487 reviews
Top guest favourite
Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 265 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
9–14 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, No bathroom
20–25 Sept
4.98 out of 5 average rating, 524 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
Cabin in Rileyville
Ukiah Mountain Retreat
2 bedrooms, 5 beds, 2 bathrooms
23–28 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
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
7–12 Aug
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Flat in The Plains
Rose End
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 713 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
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, 750 reviews
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 538 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
8–13 Aug
4.99 out of 5 average rating, 265 reviews
Top guest favourite
Room in Shepherdstown
Little Big Sky! A cozy bedroom in the country!
1 queen bed, 1 bathroom
8–13 Aug
4.97 out of 5 average rating, 100 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, 122 reviews
Top guest favourite
Farm stay in Edinburg
Circle F Ranch Bunkhouse- Elevated Farm Stay
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews