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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 bed, 1 private bathroom
16–21 Aug
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4.99 out of 5 average rating, 484 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
2–7 Aug
4.97 out of 5 average rating, 354 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds
9–14 Aug
4.91 out of 5 average rating, 275 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
13–18 Aug
4.99 out of 5 average rating, 192 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds
2–7 Aug
4.98 out of 5 average rating, 221 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom
1–6 Aug
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds
4–9 Sept
4.98 out of 5 average rating, 246 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
12–17 Oct
4.94 out of 5 average rating, 66 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds
1–6 Aug
4.95 out of 5 average rating, 40 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, 160 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed
1–6 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
1 bedroom, 3 beds
16–21 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Guest suite in Clear Brook
Bluebird Bungalow
1 bedroom, 3 beds
3–8 Aug
4.97 out of 5 average rating, 73 reviews
Guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds
1–6 Aug
4.87 out of 5 average rating, 91 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds
3–8 Aug
4.98 out of 5 average rating, 55 reviews
Hotel room in Winchester
George Washington l Queen Bed l Historic Charm
1 bedroom, 1 queen bed
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds
10–15 Aug
4.92 out of 5 average rating, 175 reviews
Top guest favourite
Home in Warren County
Mountain Views w/Hot Tub, 95” TV & Trail Access
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
1 bedroom, 1 king bed
17–22 Aug
5.0 out of 5 average rating, 28 reviews