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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
19–24 Jul
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4.99 out of 5 average rating, 479 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 350 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 188 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 270 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
4.98 out of 5 average rating, 54 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
12–17 Jul
4.9 out of 5 average rating, 140 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 244 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
26–31 Jul
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
1 bedroom, 1 king bed, 1 bathroom
25–30 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
2 bedrooms, 2 queen beds, 1.5 bathrooms
12–17 Jul
4.94 out of 5 average rating, 51 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
13–18 Jul
4.93 out of 5 average rating, 242 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
4.96 out of 5 average rating, 158 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed, 1.5 bathrooms
14–19 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 133 reviews
Top guest favourite
Home in Winchester
Misty Meadow has quite setting in the country.
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Aug
4.93 out of 5 average rating, 89 reviews
Guest favourite
Flat in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 bedrooms, 2 beds, 2 bathrooms
21–28 Jul
4.88 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
13–18 Jul
4.95 out of 5 average rating, 39 reviews
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds, 1 bathroom
15–22 Aug
4.72 out of 5 average rating, 75 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
4.97 out of 5 average rating, 118 reviews