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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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

Downtown Apartment-  Renovated 1920s Gas Station
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath
Downtown Apartment- Renovated 1920s Gas StationBrand new refurbished gas station from 1920s repurposed into beautiful apartment. Private off-street parking with EV car charging station, full kitchen, custom shower with rain system. High speed Wi-Fi, 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, a neighborhood pizza parlor and the downtown walking mall.
Modern Upscale Home, Historic Downtown Winchester
Entire residential home · 6 guests · 3 beds · 1.5 baths
Modern Upscale Home, Historic Downtown WinchesterNEW to Airbnb! Experience all the charm that downtown Winchester has to offer in this Old Town historic district home with modern flair. Just steps away from the home of country music legend Patsy Cline and a few minutes' stroll from the Winchester walking mall, the upscale style and amenities of this home can't be beat. Charming interiors, private parking, and outdoor front porch and patio spaces make this a unique find for couples, families, or groups of friends visiting the area.
Modern Elegance in Historic Old Town Winchester
Entire townhouse · 4 guests · 2 beds · 1.5 baths
Modern Elegance in Historic Old Town WinchesterJust 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.

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Popular amenities for Winchester vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Winchester

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Immerse yourself in Old Town Winchester
$79 per night
  1. Entire townhouse
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Little Blue Cork
$172 per night
SUPERHOST
  1. Entire rental unit
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Pretty Little Apt by the Train II
$90 per night
SUPERHOST
  1. Entire rental unit
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The Blue Door steps from Handley Library
$79 per night
SUPERHOST
  1. Entire rental unit
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Downtowner
$118 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Escape to Blossom, a EuroLux MidCentury Experience
$134 per night
SUPERHOST
  1. Entire residential home
  2. Winchester
Historic District Charm On Cameron Street
$152 per night
SUPERHOST
  1. Tiny house
  2. Winchester
Zen Garden Art Studio Tiny Home
$145 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Merrimans Meadow
$115 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
The Stock Exchange downtown 3rd floor studio apt
$85 per night
SUPERHOST
  1. Entire residential home
  2. Winchester
Indigo Blue modern open vibe on tree lined street
$188 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Drayton II Studio walk to downtown
$75 per night