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Winchester
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Over 1,000 places in Winchester
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
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
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)
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
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, 263 reviews
4.94 (263)
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
Home in Winchester
Newly Renovated Cozy Cottage
1 queen bed
1 queen bed
Apr 14 – 19
Apr 14 – 19
$79
night
$79 per night
4.9 out of 5 average rating, 180 reviews
4.9 (180)
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
1 bed
1 bed
Apr 10 – 15
Apr 10 – 15
$75
night
$75 per night
4.71 out of 5 average rating, 563 reviews
4.71 (563)
Guest favorite
Guest favorite
Place to stay in Winchester
Crash Landing
1 bed
1 bed
Apr 6 – 11
Apr 6 – 11
$65
night
$65 per night
4.86 out of 5 average rating, 35 reviews
4.86 (35)
Guest favorite
Guest favorite
Apartment in Winchester
Rosamond downtown studio apt w/free parking
1 bed
1 bed
Apr 1 – 6
Apr 1 – 6
$99
night
$99 per night
4.85 out of 5 average rating, 41 reviews
4.85 (41)
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)
Guest favorite
Guest favorite
22
Reviews
5.0
Rating
1
Year hosting
Room in Winchester
Stay with Laís
Stay with Laís
Cozy Private Bedroom in Old Town Winchester
Apr 1 – 6
Apr 1 – 6
$45
night
$45 per night
5.0 out of 5 average rating, 22 reviews
5.0 (22)
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
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
$90
night
$90 per night
4.92 out of 5 average rating, 51 reviews
4.92 (51)
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
Apartment in Winchester
Downtowner
3 beds
3 beds
Apr 21 – 26
Apr 21 – 26
$120
night
$120 per night
4.98 out of 5 average rating, 214 reviews
4.98 (214)
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
Cottage in Winchester
Lockley Cottage at Historic Perry Farm
2 beds
2 beds
Jun 18 – 23
Jun 18 – 23
$84
night
$84 per night
4.89 out of 5 average rating, 94 reviews
4.89 (94)
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