Search results; Over 1,000 homes in Winchester

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Guest favorite
Apartment in Winchester
Scarborough Fair walk to downtown two story apt
8 guests3 bedrooms6 beds1 bath
Sep 21 – 26
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Sep 21 – 26
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ﺩ.ﺇ5,188 for 5 nights

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Guest favorite
Apartment in Winchester
Home Away from Home
1 queen bed
Oct 2 – 7
ﺩ.ﺇ1,882 for 5 nights
4.88 out of 5 average rating, 43 reviews
Top guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
Oct 12 – 17
ﺩ.ﺇ2,786 for 5 nights
4.93 out of 5 average rating, 259 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 queen bed
Sep 20 – 25
ﺩ.ﺇ2,903 for 5 nights, originally ﺩ.ﺇ3,291
5.0 out of 5 average rating, 223 reviews
Top guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 queen beds
Sep 21 – 26
ﺩ.ﺇ4,176 for 5 nights
4.98 out of 5 average rating, 206 reviews
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Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
3 beds
Sep 21 – 26
ﺩ.ﺇ1,598 for 5 nights
4.72 out of 5 average rating, 674 reviews
Guest favorite
Apartment in Winchester
Historic French Modern Downtown
1 queen bed
Sep 27 – Oct 2
ﺩ.ﺇ2,256 for 5 nights
4.88 out of 5 average rating, 17 reviews
Top guest favorite
Home in Winchester
Cozy Cottage
1 queen bed
Nov 16 – 21
ﺩ.ﺇ2,045 for 5 nights
4.91 out of 5 average rating, 286 reviews
Top guest favorite
Home in Winchester
Downtown Chic Condo w/parking
Sep 28 – Oct 3
ﺩ.ﺇ3,044 for 5 nights
5.0 out of 5 average rating, 67 reviews
Top guest favorite
Room in Stephens City
Stay with Clara
Room in Quiet Neighborhood
Sep 19 – 24
ﺩ.ﺇ1,038 for 5 nights
4.97 out of 5 average rating, 39 reviews
Superhost
Apartment in Winchester
Nostalgia Lane 3 BR in the heart of the city
3 beds
Sep 21 – 26
ﺩ.ﺇ3,961 for 5 nights
4.89 out of 5 average rating, 214 reviews
Guest favorite
Cabin in Capon Bridge
Mountain Top Cabin
4 beds
Sep 21 – 26
ﺩ.ﺇ3,186 for 5 nights
4.96 out of 5 average rating, 83 reviews
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
1 queen bed
Oct 25 – 30
ﺩ.ﺇ3,686 for 5 nights
4.96 out of 5 average rating, 110 reviews
Top guest favorite
Apartment in Winchester
Peaceful Family Retreat in the Heart of Winchester
3 beds
Oct 28 – Nov 2
ﺩ.ﺇ2,002 for 5 nights
5.0 out of 5 average rating, 55 reviews
Top guest favorite
Boutique hotel in Capon Bridge
Sassafras Suite ~ 1 of 5 Unique Stays at Basswood
1 queen bed
Sep 19 – 24
ﺩ.ﺇ1,723 for 5 nights
4.99 out of 5 average rating, 115 reviews
Top guest favorite
Tiny home in Stephens City
Farm Stay in a luxury tiny home
1 bed
Nov 4 – 9
ﺩ.ﺇ3,203 for 5 nights
5.0 out of 5 average rating, 6 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Oct 20 – 25
ﺩ.ﺇ2,200 for 5 nights
4.91 out of 5 average rating, 113 reviews
Apartment in Berkeley County
Private basement unit Bunker Hill, WV (WV-VA line)
1 bed
Sep 19 – 24
ﺩ.ﺇ1,688 for 5 nights, originally ﺩ.ﺇ2,048
New place to stay
Guest favorite
Home in Winchester
Historic District Charm On Cameron Street
3 beds
Oct 30 – Nov 4
ﺩ.ﺇ3,122 for 5 nights, originally ﺩ.ﺇ3,397
4.93 out of 5 average rating, 159 reviews