Find Luxury Hotels in Old Town Winchester, VA

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Old Town Winchester Luxury Hotels

Tonight
21 Jul - 22 Jul
Tomorrow
22 Jul - 23 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Top Old Town Winchester Luxury Hotels

The George Washington Hotel, A Wyndham Grand Hotel
2 restaurants, breakfast, lunch, dinner served; American cuisine

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1006)
"Historical hotel in heart of Winchester, steps from Old Town. Really felt
luxurious
~ credit to all involved. Keep up the good work."
Carolyn
The price is SAR 475
SAR 538 total
includes taxes & fees
28 Jul - 29 Jul
The George Washington Hotel, A Wyndham Grand Hotel
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.

Top Old Town Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Breakfast was good. Well stocked and fresh"
Travis 1-night trip
Posted 4 days ago
La Quinta Inn & Suites by Wyndham Winchester

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 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.