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.
La Quinta Inn & Suites by Wyndham Winchester
Clean, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience.
Reviewed on 31 Jan 2026
Travelodge by Wyndham Winchester
Room was great and breakfast was ok but had waffles
Reviewed on 2 Feb 2026
The George Washington Hotel, A Wyndham Grand Hotel
Clean nice room Great location for restaurants
Reviewed on 28 Jan 2026
Star view cabin-Riverfront
We came during an unexpected snow storm and still had the best time. She came over to introduce herself to us and was absolutely amazing, welcoming, and accommodating to our needs during the storm and offered us an extra night if we got stuck. The cabin was the perfect size with the best Mountain ...
Reviewed on 25 Jan 2026
Dreamtime - Modern A-frame Cabin w/ Hot tub
Lovely little cabin on a wooded lot. Loved the wood stove and the hot tub. Such a relaxing experience.
Reviewed on 18 Jan 2026
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Jackie was exceptionally communicative and collaborative regarding our trip that would be disrupted by the recent snow storm. I really appreciate how detailed Jackie was, how she checked in with me regularly and worked with me so that I could still enjoy the beautiful rental for a night before the ...
Reviewed on 27 Jan 2026
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.
Jim Barnett Park
Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.
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.
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.
Patsy Cline Historic House
You can find out about the history of Winchester with a stop at Patsy Cline Historic House. 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.
