Old Town Winchester Travel Guide
Winchester
Visit Old Town Winchester
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 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.
Bright Box Theater
Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.
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.
Old Court House Civil War Museum
You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
Fantastic
Reviewed on 19 Feb 2026
La Quinta Inn & Suites by Wyndham Winchester
Clean room. Comfortable bed. Easy in and out. Reasonably close to Old Town Winchester in historic district. Friendly staff.
Reviewed on 1 Mar 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Staff very friendly, hotel very clean, rooms, bathrooms clean and spacious. Only small issue is carpet on 4th floor just off of the elevator area is stretched and loose tripping hazard. Otherwise really a great place to stay
Reviewed on 1 Mar 2026
TownePlace Suites by Marriott Front Royal
Don’t stay here ICE is staying here
Reviewed on 20 Feb 2026
Sleep Inn & Suites Winchester near University
Hotel needs updating and repair. Had hole in bathroom door and securiity latch was broken.
Reviewed on 23 Feb 2026
Hampton Inn Winchester-University/Mall Area
I sent a message to the Hotel as we had to head directly home - as my wife was feeling ill; but I'm not sure the Hotel received my message and canceled the reservation. I'm surprised I didn't get a response.
Reviewed on 18 Feb 2026
Other neighbourhoods around Old Town Winchester
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.
