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Search results; Over 1,000 homes in Winchester

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, 209 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
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
Home in Winchester
Chateau Briede vineyard hot tub
4 bedrooms, 4 beds, 3.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 3 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
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
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
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
28 Sept – 5 Oct
4.88 out of 5 average rating, 26 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 80 reviews
Top guest favourite
Home in Inwood
Farm-Lane Retreat w/ Game Room • 1 Min to I-81
3 bedrooms, 6 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 36 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
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
Top guest favourite
Home in Martinsburg
Architectural Mountaintop Retreat | Shenandoah
4 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Religious building in Stephens City
The Sanctuary in the Shenandoah Valley
3 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 136 reviews