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
Room was clean but a lil noisy. We didn't have the best room location. Must have been close to a staff area
Reviewed on 2 Mar 2026
La Quinta Inn & Suites by Wyndham Winchester
Great hotel stay for our trip down soutg! Very clean and very nice rooms- very quiet!
Reviewed on 6 Mar 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Yes
Reviewed on 3 Mar 2026
TownePlace Suites by Marriott Front Royal
Room was amazing like always. Will stay there again.
Reviewed on 4 Mar 2026
Sleep Inn & Suites Winchester near University
This Sleep Inn is not clean or well maintained. A sofa in our room, 318, was stained, torn upholstery and dirty.. The parking lot was dark at night, with sparse and broken lights. The ice machine was dirty with no ice available. The elevator had no inspection certificate.. Expedia should not include ...
Reviewed on 5 Mar 2026
Hampton Inn Winchester-University/Mall Area
All good. Clean, nice hotel for us, a one night stay for traveling.
Reviewed on 4 Mar 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.
