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Search results; Over 1,000 places in Winchester
Over 1,000 places in Winchester
Guest favorite
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
2 beds
May 6 – 11
May 6 – 11
$104
night
$104 per night
4.95 out of 5 average rating, 164 reviews
4.95 (164)
Guest favorite
Guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 queen bed
1 queen bed
Apr 5 – 10
Apr 5 – 10
$147
$125
night
$125 per night, originally $147
5.0 out of 5 average rating, 134 reviews
5.0 (134)
Guest favorite
Guest favorite
Apartment in Winchester
Downtown 1920's Gas Station
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
$111
night
$111 per night
4.94 out of 5 average rating, 264 reviews
4.94 (264)
Guest favorite
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
$85
night
$85 per night
4.96 out of 5 average rating, 45 reviews
4.96 (45)
Guest favorite
Guest favorite
Apartment in Winchester
Modern Twist in Old Town! Rock n' Roll FUN!
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
$109
night
$109 per night
4.89 out of 5 average rating, 101 reviews
4.89 (101)
Guest favorite
Guest favorite
Cottage in Winchester
Emma's Stone Cottage
3 beds
3 beds
Apr 7 – 12
Apr 7 – 12
$109
night
$109 per night
4.97 out of 5 average rating, 417 reviews
4.97 (417)
Guest favorite
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
1 queen bed
1 queen bed
Apr 2 – 7
Apr 2 – 7
$140
night
$140 per night
4.97 out of 5 average rating, 75 reviews
4.97 (75)
Home in Winchester
Downtown Chic Condo w/parking
Apr 4 – 9
Apr 4 – 9
$104
night
$104 per night
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favorite
Guest favorite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
$179
night
$179 per night
4.92 out of 5 average rating, 36 reviews
4.92 (36)
Guest favorite
Guest favorite
Cabin in Winchester
Kona's Cabin — Pet Friendly, King Bed, Fireplace
4 beds
4 beds
Apr 7 – 12
Apr 7 – 12
$129
night
$129 per night
4.89 out of 5 average rating, 54 reviews
4.89 (54)
Guest favorite
Guest favorite
Apartment in Winchester
Dreamweaver Bright 1BR 2 blocks to Walking Mall
1 bed
1 bed
Apr 1 – 6
Apr 1 – 6
$122
night
$122 per night
4.87 out of 5 average rating, 30 reviews
4.87 (30)
Guest favorite
Guest favorite
Home in Winchester
City Charmer minutes from Old Town
2 beds
2 beds
Apr 3 – 8
Apr 3 – 8
$109
night
$109 per night
4.97 out of 5 average rating, 210 reviews
4.97 (210)
Guest favorite
Guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
2 beds
2 beds
Apr 7 – 12
Apr 7 – 12
$160
night
$160 per night
4.98 out of 5 average rating, 52 reviews
4.98 (52)
Guest favorite
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
$214
night
$214 per night
4.93 out of 5 average rating, 148 reviews
4.93 (148)
Home in Winchester
Historic District Charm On Cameron Street
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
$135
night
$135 per night
4.94 out of 5 average rating, 116 reviews
4.94 (116)
Guest favorite
Guest favorite
Cottage in Winchester
Uber SXY Private Country Escape! Hot Tub & Views~
1 queen bed
1 queen bed
May 29 – Jun 3
May 29 – Jun 3
$208
night
$208 per night
4.98 out of 5 average rating, 296 reviews
4.98 (296)
Guest favorite
Guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 queen beds
2 queen beds
Apr 21 – 26
Apr 21 – 26
$178
night
$178 per night
4.97 out of 5 average rating, 163 reviews
4.97 (163)
Guest favorite
Guest favorite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
$295
night
$295 per night
5.0 out of 5 average rating, 18 reviews
5.0 (18)
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