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Search results; Over 1,000 homes in Winchester

Top guest favourite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
1 bedroom, 2 beds, 1.5 private bathrooms
7–12 Sept
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4.93 out of 5 average rating, 313 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, 198 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
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 488 reviews
Top guest favourite
Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
1 bed, 1 bathroom
15–20 Aug
4.97 out of 5 average rating, 184 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, 248 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
15–20 Aug
4.93 out of 5 average rating, 248 reviews
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
4.95 out of 5 average rating, 206 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, 154 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, 526 reviews
Guest favourite
Tiny home in Harpers Ferry
Romantic & Fun w/Amazing Overlook & Hot Tub
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 208 reviews
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.97 out of 5 average rating, 271 reviews
Top guest favourite
Cabin in Rileyville
Ukiah Mountain Retreat
2 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 125 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
21–26 Aug
4.98 out of 5 average rating, 122 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
Cabin in Fort Valley
Hidden in Shenandoah Valley|Pool|Pets|Fire Pit
1 bedroom, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 141 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, 232 reviews
Top guest favourite
Home in Inwood
The Inwood House- easy on/off I-81
2 bedrooms, 2 queen beds, 1 bathroom
3–8 Sept
4.95 out of 5 average rating, 567 reviews