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 top-notch restaurants or cosy cafes 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 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.
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.
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
Wonderful stay.
Reviewed on 17 Oct 2025

Travelodge by Wyndham Winchester
My room wasnt cleaned for 2 days but everything else was awesome
Reviewed on 18 Oct 2025

La Quinta Inn & Suites by Wyndham Winchester
It was great the only thing bad .Breakfast only started at 7 am we had to leave at 6.30 am
Reviewed on 18 Oct 2025

Hampton Inn Winchester-University/Mall Area
Parking area felt very safe. Fruit available for breakfast.
Reviewed on 21 Oct 2025

Comfort Inn & Suites Winchester
Convenient location, clean, reasonable price
Reviewed on 17 Oct 2025

Microtel Inn & Suites by Wyndham Winchester
Great little hotel if of I81. Very friendly staff and streamlined service. Darci was exceptional. Rooms are small but very nicely appointed and clean. Hot coffee in the lobby when we arrived. Decent breakfast. Indoor pool and fitness center. Definitely recommend.
Reviewed on 16 Oct 2025
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 Winchester Little Theater.
Old Town Winchester Travel Guide
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