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Search results; Over 1,000 homes in Winchester

Guest favourite
Home in Winchester
Cozy 3BR Retreat w/ Patio, Fire Pit & Yard
3 bedrooms, 4 beds, 2 private bathrooms
15–20 Sept
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4.92 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 359 reviews
Home in Winchester
The Cozy Brick Cottage on Opequon Ave
3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Sept
4.67 out of 5 average rating, 3 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
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
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 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
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds, 3 bathrooms
20–25 Sept
4.94 out of 5 average rating, 63 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
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
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, 203 reviews
Superhost
Room in Winchester
Private Room
1 single bed, 1 bathroom
16–21 Sept
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 bathrooms
11–16 Sept
4.87 out of 5 average rating, 93 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 147 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
Cabin in Gerrardstown
The Nest: Modern Cabin Retreat on 5 Wooded Acres
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 209 reviews
Top guest favourite
Home in Winchester
Bear Drop Inn, walking trails, pond, Winchester
4 bedrooms, 7 beds, 3.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 25 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