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 Handley Regional Library.
Microtel Inn & Suites by Wyndham Winchester
This is our number one spot to stay in in Winchester. The location is perfect. Rooms are clean and modern.
Reviewed on 14 Jan 2026
La Quinta Inn & Suites by Wyndham Winchester
yes, room was spotless very nice place to stay
Reviewed on 13 Jan 2026
Travelodge by Wyndham Winchester
C'était propre et tranquille
Reviewed on 11 Jan 2026
Private, light filled retreat space...
with your own pickleball court!
The property was absolutely gorgeous! The cabin itself was extremely clean and cozy. The owners are super kind and communicative. They helped us when the gas fireplace needed to be relit! I’d definitely stay here again!!
Reviewed on 12 Jan 2026
Dreamtime - Modern A-frame Cabin w/ Hot tub
I took my Mother here for her 80th Bday getaway. It was so quiet and peaceful and relaxing. We had everything we needed. I was so impressed by the cleanliness and quaint decor of this A-Frame. The beds were wonderfully comfortable. We sat at the table and made dinners, did puzzles and listened to ...
Reviewed on 7 Dec 2025
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Cozy house in a charming village surrounded by the most beautiful views!
Reviewed on 30 Dec 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 cosy cafes or top-notch restaurants 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.
ValleyHealth Winchester Medical Center
If ValleyHealth 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.
