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Search results; Over 1,000 homes in Winchester

Top guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds, 1 private bathroom
11–16 Oct
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4.97 out of 5 average rating, 294 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
14–19 Sept
4.97 out of 5 average rating, 358 reviews
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 79 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 248 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds
13–18 Sept
4.98 out of 5 average rating, 224 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds
6–11 Sept
4.96 out of 5 average rating, 163 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds
13–18 Sept
4.91 out of 5 average rating, 278 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom
8–13 Sept
5.0 out of 5 average rating, 90 reviews
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds
15–22 Sept
4.72 out of 5 average rating, 76 reviews
Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds
7–12 Sept
4.87 out of 5 average rating, 93 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed
28 Sept – 3 Oct
4.99 out of 5 average rating, 492 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds
19–24 Sept
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Home in Winchester
Misty Meadow has quite setting in the country.
2 bedrooms, 2 beds
16–21 Sept
4.93 out of 5 average rating, 91 reviews
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds
20–25 Sept
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds
6–11 Sept
4.98 out of 5 average rating, 124 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds
20–25 Sept
4.9 out of 5 average rating, 147 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds
3–8 Sept
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed
2–7 Sept
4.93 out of 5 average rating, 250 reviews
Top guest favourite
Home in Martinsburg
Charming Home Explore, Relax, and Enjoy
4 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 23 reviews