Winchester, VA
Travel Guide
Visit Winchester
Where to stay in Winchester
Old Town Winchester
Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area.
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.
Spark by Hilton Winchester
"This was an easy to get to property. There was plenty of walk to restaurants nearby. Everyone was friendly and helpful. Breakfast was basic but plentiful."
Reviewed on 23 June 2026
TRU By Hilton Winchester
"It was the cleanest hotel I have ever stayed at. The property was well maintained. Free breakfast was good. I will stay there every time I pass through Winchester. The hotel looked like it was built and opened yesterday. Lol! Maybe that’s why everything was so clean. Only time will tell. And the ..."
Reviewed on 23 June 2026
The George Washington Hotel, A Wyndham Grand Hotel
"Enjoyed the stay here for a weekend exploring the Shenandoah Valley."
Reviewed on 23 June 2026
Private, light filled retreat space...
with your own pickleball court!
"We had a wonderful stay! The home was clean, comfortable, and exactly as described. The host made everything very easy. We would definitley stay here again and highly recommend it."
Reviewed on 14 June 2026
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
"The house was very clean and comfortable. Very close to town."
Reviewed on 11 June 2026
Dreamtime - Modern A-frame Cabin w/ Hot tub
"I found the atmosphere cozier and lovely. I really liked it."
Reviewed on 8 June 2026
Popular places to visit
Museum of the Shenandoah Valley
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses 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. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Shenandoah University
Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.
Apple Blossom Mall
You can enjoy retail therapy at Apple Blossom Mall during your visit to Winchester. While in this walkable area, you can savor 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 savor the top-notch restaurants.
Winchester Little Theater
Enjoy a show at Winchester Little Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
