Old Town Winchester Travel Guide
Tourist Guide
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 top-notch restaurants or cosy cafes 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.
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.
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.
Our pick of the best Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
Location of hotel is great for walking to restaurants and shops.
Reviewed on 18 Mar 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service.
Reviewed on 23 Mar 2026
La Quinta Inn & Suites by Wyndham Winchester
Room was clean, lobby and staff friendly. This is our second time staying so we always enjoy coming.
Reviewed on 23 Mar 2026
Sleep Inn & Suites Winchester near University
The room was very clean. The staff are friendly. Nice place to stay.
Reviewed on 23 Mar 2026
Microtel Inn & Suites by Wyndham Winchester
The check in attendant seemed disengaged. Disappointed internet connection was not secured. Breakfast not even worth eating.
Reviewed on 24 Mar 2026
Hampton Inn Winchester-University/Mall Area
Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel
Reviewed on 15 Mar 2026
Check Old Town Winchester hotel availability
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.
