A white neoclassical building with columns, an American flag, and a clock tower.

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Check availability on Old Town Winchester Luxury Hotels

Our top choices for Old Town Winchester luxury hotels

A traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.

1. Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (692 reviews)
The price is ฿4,980
฿6,413 total
includes taxes & fees
8 Nov - 9 Nov
Hillbrook Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Old Town Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Whooooo!"
Lauren 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Old Town Winchester?
Let Expedia help you arrange your flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport or Washington Dulles International Airport (IAD) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Old Town Winchester has to offer. During your visit, you might want to enjoy the restaurants and bars which Old Town Winchester is known for.
What's there to see and do in Old Town Winchester?
Enjoy all that Old Town Winchester has to offer when you visit Bright Box Theater, Shenandoah Valley Discovery Museum and Old Court House Civil War Museum. If you have extra time while you're in the area, you might want to stop by Handley Regional Library and George Washington's Office.