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Search results; Over 1,000 homes in Winchester

Guest favourite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
1 bedroom, 2 beds, 1.5 private bathrooms
13–18 Aug
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4.93 out of 5 average rating, 307 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 479 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 352 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 189 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
14–19 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
4.96 out of 5 average rating, 158 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 271 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 140 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 245 reviews
Superhost
Cabin in Great Cacapon
New Listing! Riverfront Home w/ Hot Tub & Fire Pit
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 201 reviews
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
2 bedrooms, 2 queen beds, 1.5 bathrooms
9–14 Aug
4.94 out of 5 average rating, 53 reviews
Top guest favourite
Home in Clear Brook
Sunrise/Sunset Views
4 bedrooms, 5 beds, 2.5 bathrooms
21–26 Jul
5.0 out of 5 average rating, 10 reviews
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
14–19 Jul
4.95 out of 5 average rating, 39 reviews
Guest favourite
Home in Millwood
Peony Place renovated farmhouse in horse country
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cabin in Luray
NEWCabin Retreat | Hot Tub, Fireplace & Fire Pit
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 bedrooms, 2 beds, 2 bathrooms
21–28 Jul
4.88 out of 5 average rating, 25 reviews
Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
4.98 out of 5 average rating, 571 reviews