Winchester Travel Guide
Tourist Guide
Visit Winchester
Where to stay in Winchester
Old Town Winchester
Old Town Winchester is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum.
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.
Travelodge by Wyndham Winchester
Clean and comfortable.
Reviewed on 23 Nov 2025
La Quinta Inn & Suites by Wyndham Winchester
Safe parking. Pet friendly
Reviewed on 22 Nov 2025
Microtel Inn & Suites by Wyndham Winchester
Room and public areas were very clean and well taken care of.
Reviewed on 26 Nov 2025
Canal Cabins
The cabin was cozy and the workplace met my needs. A couple of suggestions: Tissues in the room would be nice. In Cabin 3, the chairs are missing screws on the chair cushions. Can always use more hooks on the walls for hanging: towels, jackets, clothes
Reviewed on 10 Nov 2025
Roadhaven 1830
Everything was wonderful!
Reviewed on 3 Nov 2025
Popular places to visit
Museum of the Shenandoah Valley
You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.
Shenandoah University
Enjoy the student vibe when you visit Shenandoah University during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.
Winchester Medical Center
If Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester.
Apple Blossom Mall
You can search for that perfect souvenir at Apple Blossom Mall during your stay in Winchester. While in this walkable area, you can savour the top-notch restaurants.
Shenandoah Valley Discovery Museum
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.
