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Search results; Over 1,000 homes in Winchester

Guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 private bathrooms
1–6 Aug
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4.87 out of 5 average rating, 91 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 354 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 483 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
4.91 out of 5 average rating, 274 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 192 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
4.98 out of 5 average rating, 246 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 221 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, 159 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
4–9 Aug
4.98 out of 5 average rating, 120 reviews
Top guest favourite
Home in Warren County
Mountain Views w/Hot Tub, 95” TV & Trail Access
3 bedrooms, 4 beds, 3.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
2–7 Aug
4.9 out of 5 average rating, 142 reviews
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
4.92 out of 5 average rating, 175 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 206 reviews
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Home in Winchester
Bear Drop Inn, walking trails, pond, Winchester
4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
2 bedrooms, 2 queen beds, 1 bathroom
30 Nov – 5 Dec
4.97 out of 5 average rating, 123 reviews
Top guest favourite
Religious building in Stephens City
The Sanctuary in the Shenandoah Valley
3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
4.96 out of 5 average rating, 136 reviews
Top guest favourite
Cabin in Luray
NEWCabin Retreat | Hot Tub, Fireplace & Fire Pit
2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 14 reviews