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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
13–18 Aug
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4.93 out of 5 average rating, 309 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, 481 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 353 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, 203 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Aug
4.98 out of 5 average rating, 246 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
3–8 Aug
4.99 out of 5 average rating, 191 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
4.97 out of 5 average rating, 119 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
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Winchester
Winchester farm
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
1 bedroom, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 76 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
Guest favourite
Home in Winchester
Modern Mountain House with Hot Tub & Views
3 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Berryville
Deer Chase
3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
4.99 out of 5 average rating, 112 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, 121 reviews
Guest favourite
Home in Millwood
Peony Place renovated farmhouse in horse country
2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 7 reviews