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Search results; Over 1,000 homes in Winchester

Guest favourite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
1 bedroom, 2 beds, 1.5 private bathrooms
14–19 Aug
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4.93 out of 5 average rating, 312 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, 487 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
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed
9–14 Aug
4.93 out of 5 average rating, 246 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, 266 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
Cabin in Rileyville
Ukiah Mountain Retreat
2 bedrooms, 5 beds
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Boutique hotel in Capon Bridge
Paw Paw Suite ~ 1 of 5 Unique Stays at Basswood
1 bedroom, 1 queen bed
16–21 Aug
4.99 out of 5 average rating, 266 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
Cabin in Great Cacapon
Modern Black A-Frame Retreat in the Woods
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Room in Martinsburg
Wild & Wonderful -built in 1890
1 double bed
13–18 Aug
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Flat in The Plains
Rose End
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 713 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, 482 reviews
Top guest favourite
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bedroom, 1 bed
9–14 Aug
4.95 out of 5 average rating, 125 reviews
Top guest favourite
Room in Shepherdstown
Little Big Sky! A cozy bedroom in the country!
1 queen bed
15–20 Aug
4.97 out of 5 average rating, 100 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
Farm stay in Warrenton
Winters Retreat Farm Cottage - Entire house
1 bedroom, 3 beds
3–8 Oct
4.97 out of 5 average rating, 751 reviews