Winchester Travel Guide
Tourist Guide
Visit Winchester
Our guide on 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.
TRU By Hilton Winchester
"Amazing hotel, allowed me to check in early. Very nice and clean rooms"
Reviewed on 3 June 2026
Spark by Hilton Winchester
"Staff was very nice"
Reviewed on 2 June 2026
Travelodge by Wyndham Winchester
"The room was very clean and the staff was friendly."
Reviewed on 2 June 2026
Private, light filled retreat space...
with your own pickleball court!
"We loved our stay! Very private and clean. We even tried pickleball for the first time. Would highly recommend!"
Reviewed on 31 May 2026
Dreamtime - Modern A-frame Cabin w/ Hot tub
"Great cabin! Hot tub was nice, house was very clean"
Reviewed on 14 May 2026
Roadhaven1830
"Very clean close to every and anything local food was amazing and host had a book that showed a lot about the area which came in handy and grounds was so nice games was fun and pit was amazing bed was so comfortable shower pressure was great water was nice an hot too will come back"
Reviewed on 12 Apr 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 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.
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.
Winchester Little Theater
Enjoy a show at Winchester Little Theater, a popular theatre in 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.
