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Search results; Over 1,000 places

Superhost
Room in Winchester
1-bedroom for rent in a beautiful residential home
7-min walk
10–15 May
4.82 out of 5 average rating, 56 reviews
Guest favourite
Guest suite in Winchester
Safe, cozy oasis with private living & bath.
6-min walk
27 Apr – 2 May
4.79 out of 5 average rating, 277 reviews
Guest favourite
Room in Winchester
Winchester Private Room
10-min drive
20–25 Apr
5.0 out of 5 average rating, 22 reviews
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
8-min drive
5–10 May
4.71 out of 5 average rating, 568 reviews
Guest favourite
Flat in Winchester
Downtown 1920's Gas Station
8-min drive
21–26 Apr
4.94 out of 5 average rating, 270 reviews
Guest favourite
Flat in Winchester
Newly repurposed Historic Home in Winchester VA!
11-min drive
7–12 May
4.96 out of 5 average rating, 48 reviews
Guest favourite
Home in Winchester
Newly Renovated Cozy Cottage
13-min drive
16–21 Jun
4.9 out of 5 average rating, 184 reviews
Guest favourite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
8-min drive
8–13 May
4.95 out of 5 average rating, 170 reviews
Guest favourite
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
7-min drive
13–18 May
5.0 out of 5 average rating, 137 reviews
Guest favourite
Flat in Winchester
Modern Twist in Old Town! Rock n' Roll FUN!
7-min drive
21–26 Apr
4.89 out of 5 average rating, 103 reviews
Guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
13-min drive
6–11 May
4.98 out of 5 average rating, 151 reviews
Guest favourite
Flat in Winchester
Downtowner
7-min drive
7–12 May
4.98 out of 5 average rating, 216 reviews
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
8-min drive
3–8 Jun
4.94 out of 5 average rating, 119 reviews
Guest favourite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
8-min drive
19–24 Apr
4.93 out of 5 average rating, 40 reviews
Guest favourite
Flat in Winchester
Historic Wisteria House on Old Town Walking Mall
8-min drive
20–25 Apr
4.97 out of 5 average rating, 77 reviews
Guest favourite
Flat in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
7-min drive
19–24 Apr
4.98 out of 5 average rating, 54 reviews
Guest favourite
Apartment in Winchester
Historic District Downtown Winchester
8-min drive
19–24 Apr
4.98 out of 5 average rating, 49 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
7-min drive
10–15 May
4.87 out of 5 average rating, 71 reviews