Hotels in Old Town Winchester

Search for Old Town Winchester Hotels™ Rewards

Collect 10 nights, get 1 reward night

And look out for Secret Prices on selected hotels

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

Best Old Town Winchester Hotels

Old Town Winchester overview

Old Town Winchester is a friendly place, unique for its historical sites and known for live music and museums. You'll find extensive bar and cafe options. Learn about local heritage at landmarks, such as George Washington's Office and Stonewall Jackson's Headquarters. While you're here, stop by Bright Box Theater and Old Court House Civil War Museum. If you're looking for a family-friendly getaway, Old Town Winchester is for you.

Where to stay in Old Town Winchester

Whether you're planning to stay for a night or for the week, the area around Old Town Winchester has accommodations to fit every need. Search for hotels in Old Town Winchester with by checking our online maps. These display the areas and neighbourhoods around all Old Town Winchester hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Old Town Winchester hotel deals are here with our lowest price guarantee.

How to get to Old Town Winchester

Fly in to Washington, DC (IAD-Washington Dulles Intl.), 41.6 mi (67 km) from central Old Town Winchester. Washington, DC (DCA-Ronald Reagan Washington National) is the next closest major airport, 64.6 mi (103.9 km) away.

What to see around Old Town Winchester

Family-friendly attractions include:
  • • Wilson's Wild Animal Park
  • • Appleland Sports Center
  • • Dinosaur Land
  • • Rocking S Ranch
Live music and museums stand out, with top cultural places to visit like:
  • • Bright Box Theater
  • • Old Court House Civil War Museum
  • • Shenandoah Valley Discovery Museum
  • • Winchester Little Theater
  • • Museum of the Shenandoah Valley
Distinguished for its historical sites, here are some top landmarks to visit:
  • • George Washington's Office
  • • Stonewall Jackson's Headquarters
  • • Patsy Cline Historic House
  • • Abram's Delight
  • • The Kernstown Battlefield
Here are some favourite choices:
  • • Mt Hebron Cemetery
  • • Handley Regional Library
  • • Jim Barnett Park
  • • Winchester-Frederick County Convention & Visitors Bureau
  • • Shenandoah University

When to visit Old Town Winchester

Curious about when the best time to visit is? Here are the seasonal trends to help with your planning:

Seasonal temperatures
  • January-March: 15°C day, -5°C night
  • April-June: 29°C day, 3°C night
  • July-September: 30°C day, 10°C night
  • October-December: 21°C day, -4°C night
Seasonal average rainfall
  • January-March: 214 cm
  • April-June: 276 cm
  • July-September: 262 cm
  • October-December: 225 cm
  • Historical sites
  • Shopping
  • Dining
  • Bar
  • Family-friendly
  • Romantic