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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
2 bedrooms, 3 beds, 2 private bathrooms
7–12 Nov
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4.98 out of 5 average rating, 583 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.97 out of 5 average rating, 359 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 249 reviews
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 275 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
14–19 Sept
4.98 out of 5 average rating, 224 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
30 Sept – 5 Oct
4.99 out of 5 average rating, 204 reviews
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 210 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
19–24 Sept
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 92 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 494 reviews
Top guest favourite
Home in Clear Brook
Sunrise/Sunset Views
4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 bedrooms, 2 beds, 2 bathrooms
26 Oct – 2 Nov
4.88 out of 5 average rating, 26 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Home in Winchester
Bear Drop Inn, walking trails, pond, Winchester
4 bedrooms, 7 beds, 3.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 251 reviews
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds, 1 bathroom
20–27 Sept
4.72 out of 5 average rating, 76 reviews
Guest favourite
Home in Winchester
Winchester farm
3 bedrooms, 3 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Berryville
The Hill House at Stubblefield
2 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 80 reviews
Home in Winchester
Chateau Briede vineyard hot tub
4 bedrooms, 4 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews