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Search results; Over 1,000 places in Winchester

Guest favourite
Flat in Winchester
Newly repurposed Historic Home in Winchester VA!
Hosted by Trent
1–6 Apr
4.96 out of 5 average rating, 45 reviews
Guest favourite
Place to stay in Winchester
Crash Landing
Hosted by Laura
6–11 Apr
4.86 out of 5 average rating, 35 reviews
Guest favourite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Hosted by Mona
6–11 May
4.95 out of 5 average rating, 164 reviews
Guest favourite
Room in Winchester
Stay with Laís
Cozy Private Bedroom in Old Town Winchester
1–6 Apr
5.0 out of 5 average rating, 22 reviews
Guest favourite
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
Hosted by a business
5–10 Apr
5.0 out of 5 average rating, 134 reviews
Home in Winchester
Downtown Chic Condo w/parking
Hosted by Lori
4–9 Apr
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Winchester
Downtown 1920's Gas Station
Hosted by Steve
21–26 Apr
4.94 out of 5 average rating, 263 reviews
Guest favourite
Flat in Winchester
Historic Wisteria House on Old Town Walking Mall
Hosted by Lindsey
2–7 Apr
4.97 out of 5 average rating, 75 reviews
Guest favourite
Guest suite in Winchester
Retro Vibe Studio
Hosted by Donna
1–6 Apr
4.92 out of 5 average rating, 51 reviews
Guest favourite
Flat in Winchester
Modern Twist in Old Town! Rock n' Roll FUN!
Hosted by Gillian
1–6 Apr
4.89 out of 5 average rating, 101 reviews
Guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
Hosted by a business
21–26 Apr
4.97 out of 5 average rating, 163 reviews
Home in Winchester
Historic District Charm On Cameron Street
Hosted by Elizabeth
1–6 Apr
4.94 out of 5 average rating, 116 reviews
Guest favourite
Home in Winchester
City Charmer minutes from Old Town
Hosted by Crystal
3–8 Apr
4.97 out of 5 average rating, 210 reviews
Guest favourite
Flat in Winchester
Downtowner
Hosted by Gail
21–26 Apr
4.98 out of 5 average rating, 214 reviews
Guest favourite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
Hosted by a business
1–6 Apr
4.93 out of 5 average rating, 148 reviews
Guest favourite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
Hosted by Josh
1–6 Apr
4.92 out of 5 average rating, 36 reviews
Guest favourite
Flat in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
Hosted by a business
7–12 Apr
4.98 out of 5 average rating, 52 reviews
Guest favourite
Apartment in Winchester
Historic District Downtown Winchester
Hosted by Alison
7–12 Apr
4.98 out of 5 average rating, 47 reviews