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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, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 196 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Aug
4.91 out of 5 average rating, 276 reviews
Top guest favourite
Boutique hotel in Capon Bridge
Sycamore Suite ~ 1 of 5 Unique Stays at Basswood
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.99 out of 5 average rating, 230 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
11–16 Aug
4.93 out of 5 average rating, 248 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, 525 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, 267 reviews
Top guest favourite
Home in Winchester
Misty Meadow has quite setting in the country.
2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Aug
4.93 out of 5 average rating, 90 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 161 reviews
Top guest favourite
Room in Fort Valley
Passage Creek Acres Room1-Cottage
1 queen bed, WC
16–21 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Cottage in Martinsburg
Last Rodeo Cottage
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
4.97 out of 5 average rating, 484 reviews
Top guest favourite
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bedroom, 1 bed, 1 bathroom
10–15 Aug
4.95 out of 5 average rating, 125 reviews
Top guest favourite
Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
1 bed, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 183 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
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
15–20 Aug
5.0 out of 5 average rating, 88 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, 716 reviews
Top guest favourite
Cabin in Great Cacapon
Modern Black A-Frame Retreat in the Woods
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Farm stay in Warrenton
Winters Retreat Farm Cottage - Entire house
1 bedroom, 3 beds, 1.5 bathrooms
3–8 Oct
4.97 out of 5 average rating, 751 reviews
Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 150 reviews