Search results; Over 1,000 homes in Winchester

Explore more homes

Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Sep 24 – 29
ﺩ.ﺇ1,184 for 5 nights
4.98 out of 5 average rating, 131 reviews
Top guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
Sep 7 – 12
ﺩ.ﺇ1,656 for 5 nights
4.95 out of 5 average rating, 82 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
Sep 7 – 12
ﺩ.ﺇ2,691 for 5 nights
4.93 out of 5 average rating, 253 reviews
Top guest favorite
Home in Winchester
Downtown Chic Condo w/parking
Aug 25 – 30
ﺩ.ﺇ3,066 for 5 nights
5.0 out of 5 average rating, 64 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Aug 22 – 27
ﺩ.ﺇ2,015 for 5 nights
4.91 out of 5 average rating, 111 reviews
Top guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 queen beds
Aug 22 – 27
ﺩ.ﺇ4,348 for 5 nights
4.98 out of 5 average rating, 203 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
3 beds
Sep 14 – 19
ﺩ.ﺇ1,641 for 5 nights
4.73 out of 5 average rating, 669 reviews
Guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
2 king beds
Oct 27 – Nov 1
ﺩ.ﺇ3,143 for 5 nights
4.91 out of 5 average rating, 46 reviews
Guest favorite
Apartment in Winchester
Scarborough Fair walk to downtown two story apt
6 beds
Aug 26 – 31
ﺩ.ﺇ4,628 for 5 nights
4.91 out of 5 average rating, 114 reviews
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
1 queen bed
Sep 2 – 7
ﺩ.ﺇ3,350 for 5 nights
4.96 out of 5 average rating, 108 reviews
Guest favorite
Tiny home in Harpers Ferry
Enchanting PET FREE W/Amazing ViewHot Tub Overlook
2 beds
Sep 22 – 27
ﺩ.ﺇ2,110 for 5 nights
4.97 out of 5 average rating, 138 reviews
Top guest favorite
Apartment in Stephens City
Spacious Charming Basement Apt
1 bed
Aug 21 – 26
ﺩ.ﺇ2,131 for 5 nights
5.0 out of 5 average rating, 17 reviews
Home in Winchester
Charming Home w/ Porch & Yard
4 beds
Aug 25 – 30
ﺩ.ﺇ4,478 for 5 nights
New place to stay
Superhost
Apartment in Winchester
Downtown 1920's Gas Station with Hot Tub
1 queen bed
Aug 24 – 29
ﺩ.ﺇ2,799 for 5 nights
4.9 out of 5 average rating, 362 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
3 beds
Aug 31 – Sep 5
ﺩ.ﺇ5,102 for 5 nights
4.95 out of 5 average rating, 193 reviews
Top guest favorite
Apartment in Winchester
Modern Twist in Old Town! Rock n' Roll FUN!
2 beds
Sep 12 – 17
ﺩ.ﺇ2,521 for 5 nights
4.93 out of 5 average rating, 165 reviews
Top guest favorite
Chalet in Bluemont
Emberwood | Modern Chalet + Spa + Stargazing Dome
3 beds
Sep 7 – 12
ﺩ.ﺇ7,125 for 5 nights
5.0 out of 5 average rating, 14 reviews
Top guest favorite
Apartment in Winchester
Peaceful Family Retreat in the Heart of Winchester
3 beds
Sep 7 – 12
ﺩ.ﺇ2,002 for 5 nights
5.0 out of 5 average rating, 50 reviews