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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, 308 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed
26–31 Jul
4.99 out of 5 average rating, 479 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
23–28 Jul
4.99 out of 5 average rating, 190 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
2–7 Aug
4.97 out of 5 average rating, 352 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds
18–23 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds
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
19–24 Jul
4.9 out of 5 average rating, 142 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds
1–6 Aug
4.98 out of 5 average rating, 245 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds
26–31 Jul
4.96 out of 5 average rating, 158 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds
17–22 Jul
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds
2–7 Aug
4.98 out of 5 average rating, 221 reviews
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
1 bedroom, 2 beds
19–24 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
3 bedrooms, 3 beds
3–8 Aug
4.86 out of 5 average rating, 22 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds
25–30 Oct
4.98 out of 5 average rating, 202 reviews
Top guest favourite
Cabin in Great Cacapon
New Listing! Riverfront Home w/ Hot Tub & Fire Pit
2 bedrooms, 2 beds
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
2 bedrooms, 2 queen beds
30 Nov – 5 Dec
4.97 out of 5 average rating, 121 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
26–31 Jul
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Home in Berryville
The Hill House at Stubblefield
2 bedrooms, 3 beds
17–22 Jul
4.99 out of 5 average rating, 79 reviews
Top guest favourite
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 bedroom, 1 queen bed
18–23 Jul
4.99 out of 5 average rating, 258 reviews