Old Town Winchester
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.
Things to do
Shenandoah Tour: Self-Guided Drive
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
Beautiful hotel. They just need to bring the price down a little.
Reviewed on 26 Apr 2026
Spark by Hilton Winchester
The clerk at the desk in the morning for check out was sitting on the floor behind the front desk counter with back against the wall sleeping. I’m not sure if the person was sick or tired or something much worse. I would be able to submit a photo if necessary.
Reviewed on 27 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
Place is always clean, staff is great. Convenient location
Reviewed on 27 Apr 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
The hotel and room were okay, and the breakfast was good. However, I was disappointed to find a large stain on my sheets that I didn’t notice until the morning. As far as the checkout experience. I waited about 15 minutes for someone to come to the front desk, but no one showed up. While I was standing ...
Reviewed on 27 Apr 2026
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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.
