Find Luxury Hotels in Old Town Winchester, VA

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check availability on Old Town Winchester Luxury Hotels

Pick from 1 Old Town Winchester Luxury Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

"Wonderful location and very comfortable beds"

AED 521 total

includes taxes & fees

16 Jun - 17 Jun

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Old Town Winchester?

Let Expedia help you arrange your flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport or Washington Dulles Intl. 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 need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can help you find 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 the best time to vacation in Old Town Winchester?

The hottest months are usually July and August with an average temperature of 72°F,

Coldest months: January, February, December, and March
Driest months: November, January, February, and March
Rainiest months: May, September, June, and July

What's there to see and do in Old Town Winchester?

Enjoy all that Old Town Winchester has to offer when you visit Shenandoah Valley Discovery Museum, Bright Box Theater, and Old Court House Civil War Museum. If you have extra time while you’re in the area, you might want to stop by George Washington’s Office and Handley Regional Library.