Over 1,000 places in Winchester

Guest favorite
Apartment in Winchester
Modern Twist in Old Town! Rock n' Roll FUN!
2 beds
Apr 1 – 6
4.89 out of 5 average rating, 101 reviews
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
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
Home in Winchester
Historic District Charm On Cameron Street
3 beds
Apr 1 – 6
4.94 out of 5 average rating, 116 reviews
Guest favorite
Apartment in Winchester
Downtown 1920's Gas Station
1 queen bed
Apr 21 – 26
4.94 out of 5 average rating, 263 reviews
Guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 queen bed
Apr 5 – 10
5.0 out of 5 average rating, 134 reviews
Guest favorite
Home in Winchester
Newly Renovated Cozy Cottage
1 queen bed
Apr 14 – 19
4.9 out of 5 average rating, 180 reviews
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
1 bed
Apr 10 – 15
4.71 out of 5 average rating, 563 reviews
Guest favorite
Place to stay in Winchester
Crash Landing
1 bed
Apr 6 – 11
4.86 out of 5 average rating, 35 reviews
Guest favorite
Apartment in Winchester
Rosamond downtown studio apt w/free parking
1 bed
Apr 1 – 6
4.85 out of 5 average rating, 41 reviews
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
1 queen bed
Apr 2 – 7
4.97 out of 5 average rating, 75 reviews
Guest favorite
Room in Winchester
Stay with Laís
Cozy Private Bedroom in Old Town Winchester
Apr 1 – 6
5.0 out of 5 average rating, 22 reviews
Guest favorite
Home in Winchester
City Charmer minutes from Old Town
2 beds
Apr 3 – 8
4.97 out of 5 average rating, 210 reviews
Guest favorite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
Apr 1 – 6
4.92 out of 5 average rating, 51 reviews
Guest favorite
Apartment in Winchester
Dreamweaver Bright 1BR 2 blocks to Walking Mall
1 bed
Apr 1 – 6
4.87 out of 5 average rating, 30 reviews
Guest favorite
Apartment in Winchester
Downtowner
3 beds
Apr 21 – 26
4.98 out of 5 average rating, 214 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
Cottage in Winchester
Lockley Cottage at Historic Perry Farm
2 beds
Jun 18 – 23
4.89 out of 5 average rating, 94 reviews