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
Aug 3 – 8
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Aug 3 – 8
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ﺩ.ﺇ4,779 for 5 nights

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Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
Aug 1 – 6
ﺩ.ﺇ1,021 for 5 nights
4.76 out of 5 average rating, 191 reviews
Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Aug 7 – 12
ﺩ.ﺇ1,184 for 5 nights
4.98 out of 5 average rating, 122 reviews
Guest favorite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
Aug 14 – 19
ﺩ.ﺇ2,080 for 5 nights
4.93 out of 5 average rating, 58 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
3 beds
Aug 24 – 29
ﺩ.ﺇ1,701 for 5 nights
4.73 out of 5 average rating, 665 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
Aug 10 – 15
ﺩ.ﺇ2,704 for 5 nights
4.93 out of 5 average rating, 251 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Aug 8 – 13
ﺩ.ﺇ2,075 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 1 – 6
ﺩ.ﺇ4,348 for 5 nights
4.97 out of 5 average rating, 198 reviews
Guest favorite
Home in Winchester
Cozy Cottage
1 queen bed
Aug 10 – 15
ﺩ.ﺇ2,045 for 5 nights
4.9 out of 5 average rating, 273 reviews
Guest favorite
Guest suite in Winchester
Safe, cozy oasis with private living & bath.
2 beds
Aug 3 – 8
ﺩ.ﺇ2,002 for 5 nights
4.81 out of 5 average rating, 345 reviews
Guest favorite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
3 beds
Sep 28 – Oct 3
ﺩ.ﺇ4,453 for 5 nights
4.95 out of 5 average rating, 222 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
3 beds
Aug 3 – 8
ﺩ.ﺇ5,102 for 5 nights
4.95 out of 5 average rating, 191 reviews
Guest favorite
Home in Winchester
Historic District Charm On Cameron Street
3 beds
Aug 30 – Sep 4
ﺩ.ﺇ3,444 for 5 nights
4.94 out of 5 average rating, 157 reviews
Top guest favorite
Apartment in Winchester
Peaceful Family Retreat in the Heart of Winchester
3 beds
Aug 5 – 10
ﺩ.ﺇ2,002 for 5 nights
5.0 out of 5 average rating, 48 reviews
Top guest favorite
Apartment in Winchester
Modern Twist in Old Town! Rock n' Roll FUN!
2 beds
Aug 11 – 16
ﺩ.ﺇ2,777 for 5 nights
4.93 out of 5 average rating, 163 reviews
Guest favorite
Guest suite in Stephens City
Cozy Cabin
1 queen bed
Aug 16 – 21
ﺩ.ﺇ1,981 for 5 nights
4.95 out of 5 average rating, 100 reviews
Top guest favorite
Apartment in Stephens City
Spacious Charming Basement Apt
1 bed
Aug 1 – 6
ﺩ.ﺇ2,136 for 5 nights
5.0 out of 5 average rating, 16 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
2 beds
Aug 1 – 6
ﺩ.ﺇ3,651 for 5 nights
4.98 out of 5 average rating, 110 reviews
Superhost
Room in Winchester
Stay with J ArmandoAirport,
Studio Apartment in Winchester
Aug 1 – 6
ﺩ.ﺇ1,507 for 5 nights
4.9 out of 5 average rating, 10 reviews