Old Town Winchester Travel Guide
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.
Top hotels in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel
Reviewed on 14 Jul 2025

La Quinta Inn & Suites by Wyndham Winchester
Reviewed on 13 Jul 2025

Travelodge by Wyndham Winchester
Reviewed on 17 Jul 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Reviewed on 15 Jul 2025

Comfort Inn & Suites
Reviewed on 14 Jul 2025

Microtel Inn & Suites by Wyndham Winchester
Reviewed on 16 Jul 2025
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 Winchester Little Theater.
Choose Your Old Town Winchester Hotel Style
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