Over 1,000 places

Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
5 min drive
May 7 – 12
4.96 out of 5 average rating, 49 reviews
Guest favorite
Cottage in Winchester
Uber SXY Private Country Escape! Hot Tub & Views~
10 min drive
Jun 2 – 7
4.98 out of 5 average rating, 303 reviews
Guest favorite
Apartment in Winchester
Downtown 1920's Gas Station
5 min drive
Apr 21 – 26
4.94 out of 5 average rating, 270 reviews
Guest favorite
Apartment in Winchester
Peaceful Family Retreat in the Heart of Winchester
6 min drive
Apr 21 – 26
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
9 min drive
Apr 21 – 26
4.98 out of 5 average rating, 151 reviews
Guest favorite
Cottage in Winchester
Lockley Cottage at Historic Perry Farm
18 min drive
Apr 22 – 27
4.9 out of 5 average rating, 98 reviews
Guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
5 min drive
May 13 – 18
5.0 out of 5 average rating, 137 reviews
Guest favorite
Room in Winchester
Winchester Private Room
7 min drive
Apr 20 – 25
5.0 out of 5 average rating, 22 reviews
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
5 min drive
Apr 20 – 25
4.97 out of 5 average rating, 77 reviews
Guest favorite
Home in Winchester
Newly Renovated Cozy Cottage
14 min drive
Jun 16 – 21
4.9 out of 5 average rating, 184 reviews
Guest favorite
Apartment in Winchester
Country in the Valley
11 min drive
Apr 27 – May 2
5.0 out of 5 average rating, 5 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
4 min drive
May 9 – 14
4.95 out of 5 average rating, 170 reviews
Guest favorite
Home in Winchester
Historic District Charm On Cameron Street
4 min drive
Jun 3 – 8
4.94 out of 5 average rating, 119 reviews
Guest favorite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
5 min drive
Apr 20 – 25
4.93 out of 5 average rating, 40 reviews
Guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
4 min drive
Apr 21 – 26
4.97 out of 5 average rating, 165 reviews
Guest favorite
Cottage in Winchester
Emma's Stone Cottage
22 min drive
Apr 21 – 26
4.97 out of 5 average rating, 421 reviews
Guest favorite
Cabin in High View
Mary's Cabin
34 min drive
May 12 – 17
5.0 out of 5 average rating, 44 reviews
Guest favorite
Condo in Winchester
Historic District Downtown Winchester
4 min drive
Apr 19 – 24
4.98 out of 5 average rating, 49 reviews