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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 bed, 1 private bathroom
19–24 Jul
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4.99 out of 5 average rating, 479 reviews
Top guest favourite
Flat in Winchester
Downtowner
4.97 out of 5 average rating, 351 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 189 reviews, 1 queen bed, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.9 out of 5 average rating, 270 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 158 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
4.9 out of 5 average rating, 140 reviews, 3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 54 reviews, 3 bedrooms, 5 beds, 2 bathrooms
13–18 Jul
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 244 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
4.94 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
9–14 Aug
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Guest suite in Winchester
Cozy English Basement Apt
4.64 out of 5 average rating, 61 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Jul
Guest favourite
Home in Clear Brook
Sunrise/Sunset Views
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Jul
Top guest favourite
Cabin in Luray
NEWCabin Retreat | Hot Tub, Fireplace & Fire Pit
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
4.94 out of 5 average rating, 63 reviews, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Home in Winchester
Winchester farm
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Jul
Top guest favourite
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
4.99 out of 5 average rating, 258 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Jul
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
4.98 out of 5 average rating, 221 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
4.97 out of 5 average rating, 121 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
4.95 out of 5 average rating, 39 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Jul