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Guest favorite
Condo in Winchester
Historic District Downtown Winchester
2 guests1 bedroom1 bed1 bath
May 4 – 9
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May 4 – 9
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ﺩ.ﺇ 4,456 for 5 nights
for 5 nights

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Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
3 beds
May 4 – 9
ﺩ.ﺇ 5,101 for 5 nights
for 5 nights
4.95 out of 5 average rating, 184 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
Free cancellation
May 17 – 22
ﺩ.ﺇ 3,814 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.ﺇ 3,036 for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Apartment in Winchester
Downtowner
Free cancellation
May 11 – 16
ﺩ.ﺇ 2,691 for 5 nights
for 5 nights
4.97 out of 5 average rating, 273 reviews
Top guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Free cancellation
Jun 9 – 14
ﺩ.ﺇ 3,310 for 5 nights
for 5 nights
4.98 out of 5 average rating, 99 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Jun 21 – 26
ﺩ.ﺇ 2,764 for 5 nights
for 5 nights
4.93 out of 5 average rating, 236 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
May 31 – Jun 5
ﺩ.ﺇ 3,357 for 5 nights
for 5 nights
5.0 out of 5 average rating, 202 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
May 11 – 16
ﺩ.ﺇ 2,006 for 5 nights
for 5 nights
4.91 out of 5 average rating, 98 reviews
Guest favorite
Home in Winchester
Historic District Charm On Cameron Street
3 beds
May 5 – 10
ﺩ.ﺇ 3,444 for 5 nights
for 5 nights
4.94 out of 5 average rating, 153 reviews
Guest favorite
Apartment in Winchester
Cameron Grace brand new downtown 1 BR loft
1 queen bed
May 4 – 9
ﺩ.ﺇ 3,401 for 5 nights
for 5 nights
4.92 out of 5 average rating, 13 reviews
Top guest favorite
Home in Winchester
City Charmer minutes from Old Town
Free cancellation
Jun 2 – 7
ﺩ.ﺇ 2,458 for 5 nights
for 5 nights
4.97 out of 5 average rating, 247 reviews
Top guest favorite
Home in Winchester
Downtown Chic Condo w/parking
Free cancellation
Jun 27 – Jul 2
ﺩ.ﺇ 4,056 for 5 nights
for 5 nights
5.0 out of 5 average rating, 53 reviews
Guest favorite
Apartment in Winchester
Scarborough Fair walk to downtown two story apt
6 beds
May 4 – 9
ﺩ.ﺇ 5,187 for 5 nights
for 5 nights
4.91 out of 5 average rating, 106 reviews
Top guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
May 6 – 11
ﺩ.ﺇ 1,729 for 5 nights
for 5 nights
4.97 out of 5 average rating, 67 reviews
Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
May 10 – 15
ﺩ.ﺇ 1,184 for 5 nights
for 5 nights
4.98 out of 5 average rating, 105 reviews
Top guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
Free cancellation
May 18 – 23
ﺩ.ﺇ 3,143 for 5 nights
for 5 nights
4.94 out of 5 average rating, 36 reviews
Top guest favorite
Apartment in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 queen beds
May 4 – 9
ﺩ.ﺇ 3,358 for 5 nights
for 5 nights
4.89 out of 5 average rating, 216 reviews
Superhost
Apartment in Winchester
Downtown 1920's Gas Station with Hot Tub
1 queen bed
May 4 – 9
ﺩ.ﺇ 2,908 for 5 nights
for 5 nights
4.91 out of 5 average rating, 343 reviews