Skip to main content.

Hotels in Old Town Winchester, Virginia

trover photo by Kelly Godby

Search & Compare Old Town Winchester Hotels

trover photo by Kelly Godby

Save more with Secret Prices

Get instant savings with Secret Prices

  • Pay now or later on most rooms
  • Free cancellation on most rooms
  • Price Guarantee

Best hotels in Old Town Winchester

What's Old Town Winchester Like?

There's a lot visitors like about Old Town Winchester, especially its restaurants and historical sites. Take in the local culture of Old Town Winchester at Shenandoah Valley Discovery Museum and Bright Box Theater. There's plenty more to see, including sights like George Washington's Office and Handley Regional Library.

Where are the Best Places to Stay in Old Town Winchester?

Below are the number of accommodations by star rating in Old Town Winchester and the surrounding area:

  • • 8 4-star accommodations from USD 95 per night
  • • 42 3-star accommodations from USD 78 per night
  • • 23 2-star accommodations from USD 48 per night

How to Get to Old Town Winchester

Flights to Old Town Winchester

  • • Martinsburg, WV (MRB-Eastern West Virginia Regional), 18 mi (28.9 km) from central Old Town Winchester

Things to See and Do in Old Town Winchester

What to See in Old Town Winchester

  • • George Washington's Office
  • • Handley Regional Library

Things to Do in Old Town Winchester

  • • Shenandoah Valley Discovery Museum
  • • Bright Box Theater
  • • Old Court House Civil War Museum

When Is the Best Time to Visit Old Town Winchester?

  • • Hottest months: July, June, August, September (average 84°F)
  • • Coldest months: January, February, December, March (average 25°F)
  • • Rainiest months: May, September, June, and July (average 3.69 inches of rainfall)