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Search results; Over 1,000 places

Guest favorite
Guest suite in Winchester
Safe, cozy oasis with private living & bath.
6 min walk
Apr 27 – May 2
4.79 out of 5 average rating, 277 reviews
Guest favorite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
8 min drive
Apr 19 – 24
4.93 out of 5 average rating, 40 reviews
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
8 min drive
May 5 – 10
4.71 out of 5 average rating, 568 reviews
Guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
7 min drive
May 13 – 18
5.0 out of 5 average rating, 137 reviews
Guest favorite
Apartment in Winchester
Downtown 1920's Gas Station
8 min drive
Apr 21 – 26
4.94 out of 5 average rating, 270 reviews
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
8 min drive
Apr 20 – 25
4.97 out of 5 average rating, 77 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
11 min drive
May 7 – 12
4.96 out of 5 average rating, 48 reviews
Guest favorite
Apartment in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
7 min drive
Apr 21 – 26
4.87 out of 5 average rating, 153 reviews
Guest favorite
Home in Winchester
Newly Renovated Cozy Cottage
13 min drive
Jun 16 – 21
4.9 out of 5 average rating, 184 reviews
Guest favorite
Cottage in Winchester
Lockley Cottage at Historic Perry Farm
20 min drive
Jul 15 – 20
4.9 out of 5 average rating, 98 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
8 min drive
May 8 – 13
4.95 out of 5 average rating, 170 reviews
Guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
13 min drive
May 6 – 11
4.98 out of 5 average rating, 151 reviews
Guest favorite
Home in Winchester
Historic District Charm On Cameron Street
8 min drive
Jun 3 – 8
4.94 out of 5 average rating, 119 reviews
Guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
7 min drive
Apr 19 – 24
4.98 out of 5 average rating, 54 reviews
Guest favorite
Condo in Winchester
Historic District Downtown Winchester
8 min drive
Apr 19 – 24
4.98 out of 5 average rating, 49 reviews
Guest favorite
Apartment in Winchester
Scarborough Fair walk to downtown two story apt
7 min drive
May 10 – 15
4.87 out of 5 average rating, 71 reviews
Guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
8 min drive
Apr 21 – 26
4.97 out of 5 average rating, 165 reviews
Guest favorite
Cottage in Winchester
Uber SXY Private Country Escape! Hot Tub & Views~
13 min drive
Jun 2 – 7
4.98 out of 5 average rating, 303 reviews