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Search results; Over 1,000 places in Winchester

Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
3 beds
May 5 – 10
4.71 out of 5 average rating, 568 reviews
Guest favorite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
Apr 18 – 23
4.93 out of 5 average rating, 40 reviews
Guest favorite
Apartment in Winchester
Downtown 1920's Gas Station
1 queen bed
Apr 21 – 26
4.94 out of 5 average rating, 270 reviews
Guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 queen bed
May 13 – 18
5.0 out of 5 average rating, 137 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
May 7 – 12
4.96 out of 5 average rating, 48 reviews
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
1 queen bed
Apr 20 – 25
4.97 out of 5 average rating, 77 reviews
Guest favorite
Apartment in Winchester
Country in the Valley
Apr 20 – 25
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Winchester
Newly Renovated Cozy Cottage
1 queen bed
Jun 16 – 21
4.9 out of 5 average rating, 184 reviews
Guest favorite
Cottage in Winchester
Lockley Cottage at Historic Perry Farm
2 beds
Apr 22 – 27
4.9 out of 5 average rating, 98 reviews
Guest favorite
Cottage in Winchester
Emma's Stone Cottage
3 beds
Apr 21 – 26
4.97 out of 5 average rating, 421 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
May 8 – 13
4.95 out of 5 average rating, 169 reviews
Guest favorite
Home in Winchester
City Charmer minutes from Old Town
2 beds
May 5 – 10
4.97 out of 5 average rating, 212 reviews
Guest favorite
Apartment in Winchester
Modern Twist in Old Town! Rock n' Roll FUN!
2 beds
Apr 21 – 26
4.89 out of 5 average rating, 103 reviews
Guest favorite
Condo in Winchester
Historic District Downtown Winchester
1 king bed
Apr 18 – 23
4.98 out of 5 average rating, 49 reviews
Guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4 beds
May 6 – 11
4.98 out of 5 average rating, 151 reviews
Guest favorite
Home in Winchester
Historic District Charm On Cameron Street
3 beds
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
Apr 18 – 23
4.98 out of 5 average rating, 54 reviews
Guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 queen beds
Apr 21 – 26
4.97 out of 5 average rating, 165 reviews