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Guest favorite
Home in Winchester
Enchanting Forest Retreat with Lake Views
6 guests3 bedrooms3 beds1.5 baths
Jun 1 – 6
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Jun 1 – 6
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€ 262 per night

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Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 queen bed
Apr 14 – 19
€ 160 per night
5.0 out of 5 average rating, 197 reviews
Guest favorite
Home in Winchester
Historic District Charm On Cameron Street
3 beds
Apr 13 – 18
€ 190 per night
4.94 out of 5 average rating, 150 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
Free cancellation
Apr 20 – 25
€ 85 per night
4.72 out of 5 average rating, 644 reviews
Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Apr 19 – 24
€ 63 per night
4.98 out of 5 average rating, 98 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Apr 13 – 18
€ 111 per night
4.91 out of 5 average rating, 96 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
May 4 – 9
€ 141 per night
4.93 out of 5 average rating, 231 reviews
Top guest favorite
Home in Winchester
Downtown Chic Condo w/parking
Free cancellation
May 29 – Jun 3
€ 202 per night
5.0 out of 5 average rating, 49 reviews
Top guest favorite
Apartment in Winchester
Downtowner
Free cancellation
May 9 – 14
€ 153 per night
4.97 out of 5 average rating, 269 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
2 beds
Apr 14 – 19
€ 193 per night
4.98 out of 5 average rating, 99 reviews
Top guest favorite
Home in Winchester
City Charmer minutes from Old Town
Free cancellation
May 4 – 9
€ 128 per night
4.97 out of 5 average rating, 243 reviews
Apartment in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 beds
Apr 13 – 18
€ 148 per night
New place to stay
Top guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
Apr 15 – 20
€ 99 per night
4.97 out of 5 average rating, 61 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
Free cancellation
Apr 20 – 25
€ 293 per night
4.94 out of 5 average rating, 181 reviews
Top guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
Free cancellation
May 5 – 10
€ 215 per night
4.94 out of 5 average rating, 34 reviews
Top guest favorite
Apartment in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 queen beds
Apr 13 – 18
€ 152 per night
4.89 out of 5 average rating, 211 reviews
Room in Winchester
Stay with LeroyMath teacher,
Family Friendly Retreat #5
Apr 18 – 23
€ 26 per night
4.57 out of 5 average rating, 7 reviews
Top guest favorite
Condo in Winchester
Historic District Downtown Winchester
1 king bed
Apr 15 – 20
€ 223 per night
4.99 out of 5 average rating, 75 reviews
Superhost
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
Apr 13 – 18
€ 114 per night
4.93 out of 5 average rating, 55 reviews