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Search results; Over 1,000 homes in Winchester

Flat in Winchester
Morocco Loft 2BR overlooking the city
2 bedrooms, 2 beds, 1 private bathroom
2–7 Aug
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4.73 out of 5 average rating, 63 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 483 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Winchester
Downtowner
4.97 out of 5 average rating, 354 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.91 out of 5 average rating, 274 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 192 reviews, 1 queen bed, 1 bathroom
9–14 Aug
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
4.98 out of 5 average rating, 221 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 246 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
4.9 out of 5 average rating, 143 reviews, 3 bedrooms, 6 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 159 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
4.98 out of 5 average rating, 120 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
4–9 Aug
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 55 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Warren County
Mountain Views w/Hot Tub, 95” TV & Trail Access
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
16–21 Aug
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
5.0 out of 5 average rating, 76 reviews, 1 bedroom, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4.87 out of 5 average rating, 91 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Cabin in High View
Mary's Cabin
4.98 out of 5 average rating, 206 reviews, 1 bedroom, 4 beds, 1 bathroom
25–30 Oct
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
4.92 out of 5 average rating, 52 reviews, 3 bedrooms, 3 beds, 3 bathrooms
15–20 Aug
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
5.0 out of 5 average rating, 88 reviews, 1 bedroom, 1.5 bathrooms
1–6 Aug
Guest favourite
Home in Winchester
Winchester farm
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Aug
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
4.92 out of 5 average rating, 175 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug