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Search results; Over 1,000 places in Winchester

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Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
May 6 – 11
4.95 out of 5 average rating, 164 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
Professional Host
Apr 1 – 6
4.93 out of 5 average rating, 148 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Apr 1 – 6
4.96 out of 5 average rating, 45 reviews
Guest favorite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
3 beds
Apr 1 – 6
4.92 out of 5 average rating, 36 reviews
Guest favorite
Apartment in Winchester
Downtown 1920's Gas Station
1 queen bed
Apr 21 – 26
4.94 out of 5 average rating, 264 reviews
Guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Professional Host
Apr 5 – 10
5.0 out of 5 average rating, 134 reviews
Guest favorite
Apartment in Winchester
Modern Twist in Old Town! Rock n' Roll FUN!
Individual Host
Apr 1 – 6
4.89 out of 5 average rating, 101 reviews
Home in Winchester
Downtown Chic Condo w/parking
Individual Host
Apr 4 – 9
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Winchester
City Charmer minutes from Old Town
Individual Host
Apr 3 – 8
4.97 out of 5 average rating, 210 reviews
Guest favorite
Cottage in Winchester
Emma's Stone Cottage
Individual Host
Apr 7 – 12
4.97 out of 5 average rating, 417 reviews
Home in Winchester
Historic District Charm On Cameron Street
Individual Host
Apr 1 – 6
4.94 out of 5 average rating, 116 reviews
Guest favorite
Cabin in High View
Mary's Cabin
4 beds
May 6 – 11
5.0 out of 5 average rating, 35 reviews
Guest favorite
Apartment in Winchester
Downtowner
Individual Host
Apr 21 – 26
4.98 out of 5 average rating, 214 reviews
Apartment in Winchester
Country in the Valley
Individual Host
Apr 5 – 10
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
Professional Host
Apr 21 – 26
4.97 out of 5 average rating, 163 reviews
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Individual Host
Apr 2 – 7
4.97 out of 5 average rating, 75 reviews
Guest favorite
Cottage in Winchester
Uber SXY Private Country Escape! Hot Tub & Views~
Individual Host
May 29 – Jun 3
4.98 out of 5 average rating, 296 reviews
Guest favorite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 18 reviews