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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
2 bedrooms, 3 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.98 out of 5 average rating, 576 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom
22–27 Aug
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
2 bedrooms, 3 beds
18–23 Aug
4.95 out of 5 average rating, 106 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds
18–23 Aug
4.98 out of 5 average rating, 248 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed
13–18 Sept
4.99 out of 5 average rating, 489 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds
25–30 Aug
4.98 out of 5 average rating, 223 reviews
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds
6–11 Sept
4.95 out of 5 average rating, 207 reviews
Guest favourite
Home in Winchester
Dog Friendly Mountain Retreat w/ Views & Firepit
3 bedrooms, 4 beds
23–28 Aug
4.86 out of 5 average rating, 49 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, 161 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
23–28 Aug
4.99 out of 5 average rating, 198 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds
21–26 Aug
4.98 out of 5 average rating, 122 reviews
Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds
19–24 Aug
4.87 out of 5 average rating, 93 reviews
Guest favourite
Cabin in Front Royal
Cozy Retreat near Shenandoah River HotTub•Wineries
3 bedrooms, 3 queen beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
14–19 Sept
4.97 out of 5 average rating, 357 reviews
Top guest favourite
Cabin in Great Cacapon
Modern Black A-Frame Retreat in the Woods
2 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 49 reviews
Home in Strasburg
Strasburg Cottage Hideaway | Hot Tub + Sauna
2 bedrooms, 3 beds
24–29 Aug
New place to stay
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds
6–11 Sept
4.93 out of 5 average rating, 57 reviews
Top guest favourite
Cabin in Front Royal
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
2 bedrooms, 4 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 76 reviews
Top guest favourite
Home in Inwood
The Inwood House- easy on/off I-81
2 bedrooms, 2 queen beds
3–8 Sept
4.95 out of 5 average rating, 569 reviews