Search results; Over 1,000 places in Winchester

Explore more homes

Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
Free cancellation
Jun 1 – 6
ﺩ.ﺇ5,101 for 5 nights
for 5 nights
4.95 out of 5 average rating, 185 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
2 beds
May 17 – 22
ﺩ.ﺇ3,504 for 5 nights
for 5 nights
4.98 out of 5 average rating, 102 reviews
Apartment in Winchester
Two Bdrm. Flat w/ Patio Terrace
Free cancellation
Jun 15 – 20
ﺩ.ﺇ3,036 for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Apartment in Winchester
Downtowner
3 beds
May 18 – 23
ﺩ.ﺇ2,691 for 5 nights
for 5 nights
4.97 out of 5 average rating, 273 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
3 beds
May 18 – 23
ﺩ.ﺇ1,541 for 5 nights
for 5 nights
4.72 out of 5 average rating, 649 reviews
Top guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Free cancellation
May 30 – Jun 4
ﺩ.ﺇ3,314 for 5 nights
for 5 nights
4.98 out of 5 average rating, 100 reviews
Guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
May 26 – 31
ﺩ.ﺇ1,761 for 5 nights
for 5 nights
4.97 out of 5 average rating, 67 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
May 22 – 27
ﺩ.ﺇ904 for 5 nights
for 5 nights
4.78 out of 5 average rating, 178 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
May 19 – 24
ﺩ.ﺇ2,049 for 5 nights
for 5 nights
4.91 out of 5 average rating, 99 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
May 31 – Jun 5
ﺩ.ﺇ3,357 for 5 nights
for 5 nights
5.0 out of 5 average rating, 203 reviews
Guest favorite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
Free cancellation
Jun 1 – 6
ﺩ.ﺇ4,132 for 5 nights
for 5 nights
4.95 out of 5 average rating, 79 reviews
Top guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
2 king beds
May 18 – 23
ﺩ.ﺇ3,143 for 5 nights
for 5 nights
4.94 out of 5 average rating, 36 reviews
Guest favorite
Guest suite in Winchester
Safe, cozy oasis with private living & bath.
2 beds
May 21 – 26
ﺩ.ﺇ1,722 for 5 nights
for 5 nights
4.81 out of 5 average rating, 333 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Jun 21 – 26
ﺩ.ﺇ2,785 for 5 nights
for 5 nights
4.93 out of 5 average rating, 237 reviews
Top guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
Free cancellation
Jun 15 – 20
ﺩ.ﺇ3,354 for 5 nights
for 5 nights
4.97 out of 5 average rating, 194 reviews
Guest favorite
Apartment in Winchester
Scarborough Fair walk to downtown two story apt
6 beds
May 18 – 23
ﺩ.ﺇ5,187 for 5 nights
for 5 nights
4.91 out of 5 average rating, 106 reviews
Superhost
Apartment in Winchester
"Cozy on Cameron!" - Historic Downtown Winchester
Free cancellation
Jun 2 – 7
ﺩ.ﺇ2,238 for 5 nights
for 5 nights
4.82 out of 5 average rating, 11 reviews
Guest favorite
Condo in Winchester
Historic District Downtown Winchester
Free cancellation
Jun 7 – 12
ﺩ.ﺇ4,456 for 5 nights
for 5 nights
4.99 out of 5 average rating, 77 reviews