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Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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

  1. Entire rental unit
  2. Winchester
Historic Wisteria House on Old Town Walking Mall

The historic Wisteria House is located on the Old Town Walking Mall just steps from all of the restaurants, shops, and activities that downtown Winchester has to offer. Built in ~1789 and known for the beautiful Wisteria that grows along the face of the home, it is a true piece of Winchester history.

$194 SGD per night
  1. Entire loft
  2. Winchester
Immerse yourself in Old Town Winchester

Our loft apartment is in the heart of Old Town Winchester on the Old Town Mall. Located off of a little alley, with security lighting and motion detectors you will be staying steps away from dining, shops and everything our community has to offer. Yet, our apartments are quiet and secure. Our building is OLD & has all of the charm that goes along with it. If you are looking for a sparkly new place, you may want to stay elsewhere, If you want clean, funky and awesome, we are your place!

$119 SGD per night
SUPERHOST
  1. Entire townhouse
  2. 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.

$167 SGD per night

Holiday rentals for every style

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Stay near Winchester's top sights

Photo of Museum of the Shenandoah Valley
Museum of the Shenandoah Valley28 locals recommend
Photo of Shenandoah Valley Discovery Museum
Shenandoah Valley Discovery Museum18 locals recommend
Photo of Handley Regional Library
Handley Regional Library3 locals recommend

Other great holiday rentals in Winchester

  1. Entire loft
  2. Winchester
Immerse Yourself in Old Town #3
$106 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Downtowner
$171 SGD per night
SUPERHOST
  1. Entire cottage
  2. Winchester
Escape to Foxy, Your Private Cottage at Fox Meadow
$315 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Pretty Little Apt by the Train II
$151 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Experience Basil! Modern Gem in Historic District!
$184 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Retro Loves Company
$140 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
The Loudoun Luxe
$225 SGD per night
SUPERHOST
  1. Entire apartment
  2. Winchester
Historic District Downtown Winchester
$239 SGD per night
  1. Entire rental unit
  2. Winchester
Old Town Loft In Highly Desirable Area Downtown
$220 SGD per night
  1. Entire guest suite
  2. Winchester
Luxury CLEAN MODERN w/HBOMAX, 1mi to walking mall!
$170 SGD per night
SUPERHOST
  1. Entire home
  2. Winchester
City Charmer minutes from Old Town
$175 SGD per night
  1. Entire loft
  2. Winchester
Immerse yourself in Old Town #2!
$98 SGD per night