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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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4.92 out of 5 average rating, 306 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 188 reviews, 1 queen bed, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Winchester
Downtowner
4.97 out of 5 average rating, 350 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
4.97 out of 5 average rating, 266 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 479 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
4.95 out of 5 average rating, 203 reviews, 2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 244 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
4.9 out of 5 average rating, 140 reviews, 3 bedrooms, 6 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 54 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
4.93 out of 5 average rating, 242 reviews, 1 double bed, 1.5 bathrooms
13–18 Jul
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 158 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
5.0 out of 5 average rating, 26 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
4.94 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
Top guest favourite
Cabin in High View
Mary's Cabin
4.98 out of 5 average rating, 200 reviews, 1 bedroom, 4 beds, 1 bathroom
20–25 Sept
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
4.94 out of 5 average rating, 63 reviews, 1 bed, 1 bathroom
16–21 Jul
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
31 Jul – 5 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
Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
5.0 out of 5 average rating, 133 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
14–19 Jul