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333 places in Winchester
Superhost
Cottage in Winchester
Summertime Cottage Escape! Hot Tub*Privacy*Views!
1 queen bed
Oct 29 – Nov 3
$183
night
$183 per night
4.98 (249)
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
3 beds
Oct 8 – 13
$175
night
$175 per night
4.84 (19)
Superhost
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
Oct 29 – Nov 3
$120
night
$120 per night
4.95 (133)
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester
1 bed
Nov 1 – 6
$81
night
$81 per night
4.71 (527)
Superhost
Apartment in Winchester
Rosamond downtown studio apt w/free parking
1 bed
Oct 8 – 13
$95
night
$95 per night
4.83 (29)
Superhost
Home in Winchester
Newly Renovated Cozy Cottage
1 queen bed
Oct 22 – 27
$79
night
$79 per night
4.91 (156)
Superhost
Apartment in Winchester
Escape to Blossom, a EuroLux MidCentury Experience
2 queen beds
Oct 8 – 13
$119
$101
night
$101 per night, originally $119
4.86 (135)
Superhost
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 queen bed
Oct 8 – 13
$140
night
$140 per night
5.0 (111)
Superhost
Apartment in Winchester
Magnolia Wind 1BR king w/office downtown apt
2 beds
Oct 15 – 20
$125
night
$125 per night
5.0 (14)
Superhost
Cottage in Winchester
Lockley Cottage at Historic Perry Farm
2 beds
Dec 4 – 9
$75
night
$75 per night
4.86 (73)
Superhost
Apartment in Winchester
Modern Luxe 2 Bed Apt in Old Town Winchester
2 beds
Oct 15 – 20
$145
$128
night
$128 per night, originally $145
4.89 (72)
Superhost
Home in Winchester
City Charmer minutes from Old Town
2 beds
Oct 8 – 13
$97
night
$97 per night
4.97 (193)
Superhost
Apartment in Winchester
Cleveland Park bright 2BR apt blocks from downtown
2 queen beds
Oct 15 – 20
$128
night
$128 per night
4.78 (36)
Superhost
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Oct 8 – 13
$81
night
$81 per night
4.97 (32)
Superhost
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
2 beds
Oct 15 – 20
$159
night
$159 per night
5.0 (38)
Home in Winchester
Misty Meadow Home
2 beds
Oct 3 – 8
$75
night
$75 per night
5.0 (10)
Superhost
Home in Winchester
Indigo Blue modern open vibe on tree lined street
3 beds
Oct 29 – Nov 3
$210
night
$210 per night
4.94 (131)
Place to stay in Winchester
Stay with Pepper
,
·
Customer care
Cheerful one bedroom available.
Oct 22 – 27
$35
night
$35 per night
4.73 (64)
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