Winchester
Travel 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 Winchester Little Theater.
Red Roof Inn Winchester, VA
Good stay for an overnight trip. Kumar treated us like very special people! Clean and very comfortable. Only problem - ADA shower very difficult to use for someone less then 5’4. Reaching the shower head was impossible. Would not recommend this place for special needs.
Reviewed on 22 Oct 2025
La Quinta Inn & Suites by Wyndham Winchester
Good
Reviewed on 25 Oct 2025
Comfort Inn & Suites Winchester
Amazing so clean Greta breakfast
Reviewed on 21 Oct 2025
Hidden Gem in the woods with hot tub
We loved this little cabin! It was so cozy and just 20-30 minutes from anything in town.
Reviewed on 11 Aug 2025
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Super cozy, quiet, very clean and very comfortable bed! The host was wonderful and responded to all of my questions. We will def. be back!
Reviewed on 17 Oct 2025
Dreamtime - Modern A-frame Cabin w/ Hot tub
This was a nice property. It was tucked away in the community yet very centrally located to the town and park. Private. If you have issues with mobility and are a bigger individual, this could be a challenge for a comfortable stay. The shower is located on the 2nd floor and is at best 32”x32” in ...
Reviewed on 6 Oct 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 top-notch restaurants or cosy cafes in this walkable area.
Winchester Medical Center
If Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester.
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.
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.
