Winchester vacation rentals

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Top-rated vacation rentals in Winchester

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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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Condo in Winchester

Historic District Downtown Winchester

A spacious and well appointed private apartment in the historic center of Old Town Winchester. This tastefully decorated, fully equipped and comfortable large apartment is located just one block from the walking mall, filled with quaint shops, restaurants, breweries, nightlife, galleries, and museums.

$169 per night

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Rental unit in 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.

$133 per night

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