Search results; Over 1,000 places in Winchester

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Guest favorite
Condo in Winchester
Historic District Downtown Winchester
2 guests1 bedroom1 bed1 bath
Jun 7 – 12
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Jun 7 – 12
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ﺩ.ﺇ4,456 for 5 nights
for 5 nights

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Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Jun 15 – 20
ﺩ.ﺇ1,184 for 5 nights
for 5 nights
4.98 out of 5 average rating, 107 reviews
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, 186 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
May 26 – 31
ﺩ.ﺇ2,006 for 5 nights
for 5 nights
4.91 out of 5 average rating, 101 reviews
Top guest favorite
Apartment in Winchester
Downtowner
Free cancellation
Jun 11 – 16
ﺩ.ﺇ2,777 for 5 nights
for 5 nights
4.97 out of 5 average rating, 276 reviews
Top guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Free cancellation
May 30 – Jun 4
ﺩ.ﺇ3,301 for 5 nights
for 5 nights
4.98 out of 5 average rating, 100 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
2 beds
May 28 – Jun 2
ﺩ.ﺇ3,650 for 5 nights
for 5 nights
4.98 out of 5 average rating, 103 reviews
Top guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
2 king beds
May 26 – 31
ﺩ.ﺇ3,143 for 5 nights
for 5 nights
4.95 out of 5 average rating, 38 reviews
Apartment in Winchester
Two Bdrm. Flat w/ Patio Terrace
Free cancellation
Jun 14 – 19
ﺩ.ﺇ3,036 for 5 nights
for 5 nights
4.75 out of 5 average rating, 8 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Jun 21 – 26
ﺩ.ﺇ2,790 for 5 nights
for 5 nights
4.93 out of 5 average rating, 239 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, 195 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
Jun 12 – 17
ﺩ.ﺇ3,486 for 5 nights
for 5 nights
5.0 out of 5 average rating, 203 reviews
Top guest favorite
Home in Winchester
City Charmer minutes from Old Town
Free cancellation
Jul 6 – 11
ﺩ.ﺇ2,286 for 5 nights
for 5 nights
4.97 out of 5 average rating, 251 reviews
Guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
May 26 – 31
ﺩ.ﺇ1,741 for 5 nights
for 5 nights
4.96 out of 5 average rating, 70 reviews
Guest favorite
Apartment in Winchester
Yellow Submarine trendy basement apt w/courtyard
Free cancellation
Jun 1 – 6
ﺩ.ﺇ4,112 for 5 nights
for 5 nights
4.79 out of 5 average rating, 119 reviews
Superhost
Apartment in Winchester
"Cozy on Cameron!" - Historic Downtown Winchester
Free cancellation
Jun 10 – 15
ﺩ.ﺇ2,453 for 5 nights
for 5 nights
4.82 out of 5 average rating, 11 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
Free cancellation
Jul 11 – 16
ﺩ.ﺇ1,743 for 5 nights
for 5 nights
4.72 out of 5 average rating, 649 reviews
Superhost
Apartment in Winchester
The Blue Door steps from Handley Library
1 sofa bed
May 22 – 27
ﺩ.ﺇ2,627 for 5 nights
for 5 nights
4.75 out of 5 average rating, 111 reviews
Guest favorite
Room in Stephens City
Stay with Clara
Twin Room in Quiet Neighborhood
May 22 – 27
ﺩ.ﺇ1,003 for 5 nights
for 5 nights
4.87 out of 5 average rating, 23 reviews