Old Town Winchester
Winchester
Visit Old Town Winchester
Popular places to visit
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.
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.
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.
George Washington's Office
You can find out about the history of Winchester with a visit to George Washington's Office. While in this walkable area, you can savour the top-notch restaurants.
Things to do
Shenandoah Tour: Self-Guided Drive
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
Staff was amazing! Benjamin and Carla are two of the kindest people ever!
Reviewed on 4 Jan, 2026
Microtel Inn & Suites by Wyndham Winchester
Clean room. Fan in bathroom was like an airplane engine. Breakfast didn’t start until 6:30 which meant we missed it…. On the road by 6:00….
Reviewed on 7 Jan, 2026
La Quinta Inn & Suites by Wyndham Winchester
Great
Reviewed on 4 Jan, 2026
Travelodge by Wyndham Winchester
Basic accomodations but OK for the price. Everything worked fine andd hotel easy to get to from I-81.
Reviewed on 8 Jan, 2026
Comfort Inn & Suites Winchester
We stayed twice,one night 2 weeks apart.The rooms on the parking lot side have a lot less outdoor noise, the rooms on the back of the building are against Interstate 81. We got very little sleep in the room against the highway because of constant noise from traffic. Always ask for an odd number room ...
Reviewed on 3 Jan, 2026
Quality Inn Winchester
Clean room, front dest service.
Reviewed on 5 Jan, 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.
