Search results; Over 1,000 homes in Winchester

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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, 129 reviews
Superhost
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
Aug 28 – Sep 2
ﺩ.ﺇ2,067 for 5 nights
4.93 out of 5 average rating, 58 reviews
Top guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
Sep 6 – 11
ﺩ.ﺇ1,702 for 5 nights
4.95 out of 5 average rating, 79 reviews
Top guest favorite
Condo in Winchester
Historic District Downtown Winchester
1 king bed
Aug 17 – 22
ﺩ.ﺇ2,992 for 5 nights
4.99 out of 5 average rating, 87 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
Aug 15 – 20
ﺩ.ﺇ1,090 for 5 nights
4.76 out of 5 average rating, 192 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Aug 21 – 26
ﺩ.ﺇ2,015 for 5 nights
4.91 out of 5 average rating, 111 reviews
Guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
2 king beds
Aug 25 – 30
ﺩ.ﺇ3,143 for 5 nights
4.91 out of 5 average rating, 45 reviews
Top guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 queen beds
Aug 19 – 24
ﺩ.ﺇ4,348 for 5 nights
4.98 out of 5 average rating, 203 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
Aug 19 – 24
ﺩ.ﺇ2,769 for 5 nights
4.93 out of 5 average rating, 252 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
3 beds
Aug 17 – 22
ﺩ.ﺇ5,102 for 5 nights
4.95 out of 5 average rating, 193 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
3 beds
Sep 14 – 19
ﺩ.ﺇ1,718 for 5 nights
4.73 out of 5 average rating, 669 reviews
Top guest favorite
Home in Winchester
Downtown Chic Condo w/parking
Aug 18 – 23
ﺩ.ﺇ3,104 for 5 nights
5.0 out of 5 average rating, 64 reviews
Superhost
Apartment in Winchester
Magnolia Wind 3 BR 1 BA loft… walk to downtown.
4 beds
Aug 17 – 22
ﺩ.ﺇ4,650 for 5 nights
New place to stay
Guest favorite
Room in Stephens City
Stay with Clara
Twin Room in Quiet Neighborhood
Aug 17 – 22
ﺩ.ﺇ969 for 5 nights
4.89 out of 5 average rating, 28 reviews
Guest favorite
Tiny home in Harpers Ferry
Enchanting PET FREE W/Amazing ViewHot Tub Overlook
2 beds
Oct 27 – Nov 1
ﺩ.ﺇ2,088 for 5 nights
4.97 out of 5 average rating, 136 reviews
Top guest favorite
Apartment in Stephens City
Spacious Charming Basement Apt
1 bed
Aug 14 – 19
ﺩ.ﺇ2,131 for 5 nights
5.0 out of 5 average rating, 17 reviews
Top guest favorite
Cabin in Gerrardstown
The Nest: Cozy Chalet w/Wi-Fi, Deck & Grill
3 beds
Aug 17 – 22
ﺩ.ﺇ3,244 for 5 nights
4.98 out of 5 average rating, 162 reviews
Top guest favorite
Home in Winchester
City Charmer minutes from Old Town
2 beds
Aug 24 – 29
ﺩ.ﺇ2,286 for 5 nights
4.97 out of 5 average rating, 258 reviews