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Find Luxury Hotels in Old Town Winchester, VA

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Top Old Town Winchester Luxury Hotels

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $98 per night from May 2 to May 3
4.6/5Exceptional! (982 reviews)

"The renovation of the Hotel was excellent and much of the original hotel was still present."…"

Reviewed on Apr 10, 2021

The George Washington Hotel, A Wyndham Grand Hotel
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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 4 Star Hotels in Old Town Winchester

    Hillbrook Inn

    Hillbrook Inn

    4490 Summit Point Road, Charles Town, WV
    The price is $161 per night from Apr 19 to Apr 20
    4.8/5Exceptional! (73 reviews)
    Hillbrook Inn
    L'Auberge Provencale

    L'Auberge Provencale

    13630 Lord Fairfax Hwy, White Post, VA
    The price is $199 per night from Apr 19 to Apr 20
    4.6/5Exceptional! (70 reviews)
    L'Auberge Provencale
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.

Searching for a great accommodation for your luxury trip to Old Town Winchester? Use Expedia to help you arrange a flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport or Washington, DC (IAD-Washington Dulles Intl.) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are an important consideration 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 a posh hotel with a spa, an indoor pool, or luxury bedding, Expedia can help you find the best luxury hotel experience that Old Town Winchester offers. During your visit, you might want to enjoy the restaurants and bars which Old Town Winchester is known for.

When to Visit Old Town Winchester

This is what you can expect the weather to be like while you are staying in Old Town Winchester:

  • Hottest months: July, June, August, and September, with an average temperature of 84°F
  • Coldest months: January, February, December, and March, with an average temperature of 25°F
  • Driest months: February, January, December, and October, with an average rainfall of 2.63 inches
  • Rainiest months: May, September, June, and July, with an average rainfall of 3.69 inches

Exploring Old Town Winchester

Enjoy Old Town Winchester and visit Bright Box Theater, Old Court House Civil War Museum, and Shenandoah Valley Discovery Museum. If you have a little extra time during your trip, you might want to make a stop at George Washington's Office and Mt Hebron Cemetery.

Several other things that make Old Town Winchester special are the:
  • Shopping
  • Restaurants
  • Historical sites
  • Cafés
  • Bars
  • Live music
  • Tours

More trip options

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Old Town Winchester?
During your visit, you might want to enjoy the restaurants and bars which Old Town Winchester is known for.
When can I expect good weather in Old Town Winchester?
Planning for the weather is an important factor for making your trip to Old Town Winchester a success, especially when you’re splurging. The hottest months are usually July and June with an average temp of 71°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Old Town Winchester is 38 inches.
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.