Winchester vacation rentals

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Top-rated vacation rentals in Winchester

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Rental unit in Winchester
Downtown Renovated 1920's Gas Station
Brand new refurbished gas station from 1920's repurposed into beautiful apartment. Private off-street parking/EV car charging station, full kitchen, custom shower with rain system, super high speed wifi, smart TV & Blu-Ray. Plenty of light with frosted garaged doors. AC/Heat, Washer/Dryer, Dish Washer, coffee nook, and open living design. Be a part of Old Town Winchester in this unique fun space in walking distance to breweries, neighborhood Pizzoco Pizza parlor and the downtown walking mall.
$117 per night
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Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Just a block and a half from the Old Town Winchester pedestrian mall, this historic beauty with modern elegance is sure to please. You are within walking distance of quaint shops, great restaurants, The Brightbox Theater, and The Shenendoah Discovery Museum. Spend the day touring the areas great wineries or enjoying Skyline Drive, and then return to enjoy a great night out, or an evening at home making dinner in the spacious modern kitchen.
$123 per night
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Private room in Winchester
Cheerful one bedroom available.
Take it easy at this unique and tranquil getaway! Pet friendly, with windows on northern and eastern walls. Fenced in backyard, full access to kitchen. Cats and dogs welcome.
$35 per night
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Stay near Winchester's top sights

Photo of Old Town Winchester
Old Town Winchester25 locals recommend
Photo of Walmart Supercenter
Walmart Supercenter4 locals recommend
Photo of Apple Blossom Mall
Apple Blossom Mall12 locals recommend
Photo of Costco Wholesale
Costco Wholesale3 locals recommend
Photo of Museum of the Shenandoah Valley
Museum of the Shenandoah Valley72 locals recommend
Photo of Apple Blossom Mall station
Apple Blossom Mall station14 locals recommend

Weekly rentals in Winchester

Rental unit in Winchester
Historic Wisteria House on Old Town Walking Mall
$133 per night
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Condo in Winchester
Historic District Downtown Winchester
$169 per night
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Rental unit in Winchester
Magnolia Wind brand new 1BR - 2BR /office
$141 per night
Rental unit in Winchester
Rosamond downtown studio apt w/free parking
$101 per night
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Rental unit in Winchester
Modern Luxe 2 Bed Apt in Old Town Winchester
$148 per night
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Loft in Winchester
Immerse yourself in Old Town Winchester
$70 per night
Rental unit in Winchester
The New Yorker Quiet tucked away 1BR walk to town
$124 per night
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Rental unit in Winchester
Downtowner
$123 per night
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Loft in Winchester
Immerse Yourself in Old Town #3
$65 per night
Home in Winchester
City Charmer minutes from Old Town
$120 per night
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Rental unit in Winchester
Springtime Fun! Modern Twist in Historic Downtown!
$139 per night
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Rental unit in Winchester
Easy like a Sunday Morning 1 BR apt great location
$85 per night
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