Search results; Over 1,000 homes in Winchester

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Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
Aug 1 – 6
ﺩ.ﺇ1,029 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, 123 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Aug 10 – 15
ﺩ.ﺇ2,691 for 5 nights
4.93 out of 5 average rating, 251 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
Aug 8 – 13
ﺩ.ﺇ2,071 for 5 nights
4.91 out of 5 average rating, 111 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, 347 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
Aug 8 – 13
ﺩ.ﺇ3,100 for 5 nights
5.0 out of 5 average rating, 213 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
Free cancellation
Aug 24 – 29
ﺩ.ﺇ1,701 for 5 nights
4.73 out of 5 average rating, 665 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, 199 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
Top guest favorite
Tiny home in Harpers Ferry
Enchanting PET FREE W/Amazing ViewHot Tub Overlook
Free cancellation
Oct 27 – Nov 1
ﺩ.ﺇ2,067 for 5 nights
4.98 out of 5 average rating, 132 reviews
Superhost
Apartment in Winchester
Magnolia Wind 3 BR 1 BA loft… walk to downtown.
Free cancellation
Aug 1 – 6
ﺩ.ﺇ4,960 for 5 nights
New place to stay
Guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
Free cancellation
Aug 18 – 23
ﺩ.ﺇ3,143 for 5 nights
4.93 out of 5 average rating, 43 reviews
Top guest favorite
Apartment in Stephens City
Spacious Charming Basement Apt
Free cancellation
Aug 1 – 6
ﺩ.ﺇ2,136 for 5 nights
5.0 out of 5 average rating, 16 reviews
Top guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
Aug 17 – 22
ﺩ.ﺇ1,733 for 5 nights
4.95 out of 5 average rating, 77 reviews
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Free cancellation
Sep 2 – 7
ﺩ.ﺇ3,574 for 5 nights
4.96 out of 5 average rating, 107 reviews
Guest favorite
Cabin in Star Tannery
Cabin With Wood Burning Hot Tub
2 beds
Aug 3 – 8
ﺩ.ﺇ5,024 for 5 nights
4.98 out of 5 average rating, 188 reviews
Top guest favorite
Campsite in Front Royal
Blue Mountain Hideaway • Enchanting Glamping Stay
Free cancellation
Aug 3 – 8
ﺩ.ﺇ4,305 for 5 nights
4.99 out of 5 average rating, 202 reviews
Superhost
Cabin in Wardensville
The Philosopher’s Retreat
2 beds
Aug 1 – 6
ﺩ.ﺇ3,936 for 5 nights
5.0 out of 5 average rating, 4 reviews