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Search results; Over 1,000 homes in Winchester

Guest favourite
Cabin in Winchester
Foxtrot Mokki | Secluded Getaway 2 Hours from DC
2 bedrooms, 2 beds, 2 private bathrooms
25–30 Oct
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4.96 out of 5 average rating, 179 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, 202 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 358 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, 248 reviews
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 208 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, 493 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
8–13 Sept
4.93 out of 5 average rating, 250 reviews
Superhost
Room in Winchester
Private Room
1 single bed, 1 bathroom
16–21 Sept
4.82 out of 5 average rating, 11 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 91 reviews
Home in Winchester
Chateau Briede vineyard hot tub
4 bedrooms, 4 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds, 1 bathroom
15–22 Sept
4.72 out of 5 average rating, 76 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
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, 1.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 163 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
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 129 reviews
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds, 3 bathrooms
20–25 Sept
4.93 out of 5 average rating, 61 reviews
Guest favourite
Flat in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 bedrooms, 2 beds, 2 bathrooms
28 Sept – 5 Oct
4.88 out of 5 average rating, 26 reviews
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