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 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 top-notch restaurants or cosy cafes 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 cosy cafes or top-notch restaurants in this walkable area.
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
Lovely historic hotel with wonderful views of the city and the country!
Reviewed on 28 Apr 2026
Spark by Hilton Winchester
Great 3star basic hotel. Solid pick
Reviewed on 30 Apr 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Very helpful at reception and checkin. Location was nice.
Reviewed on 28 Apr 2026
Microtel Inn & Suites by Wyndham Winchester
Exhaust fan in bathroom was incredibly loud and could not be turned off separately from the light in the bathroom. Water took a long time to become hot in the shower. Interstate traffic is very loud and the hotel walls are not well-insulated. Receipt was not provided at check-out and is not accessible ...
Reviewed on 28 Apr 2026
La Quinta Inn & Suites by Wyndham Winchester
Mmmm
Reviewed on 28 Apr 2026
Travelodge by Wyndham Winchester
Clean and friendly staff
Reviewed on 28 Apr 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.
