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
Amazing hotel with lovely rooms, easy parking, near (walking distance ) great restaurants and shops. Highly recommend spa in building.
Reviewed on 23 Oct 2025
La Quinta Inn & Suites by Wyndham Winchester
I would give a 5 star but except for the fruit flies that were in the breakfast area which the front desk said they were going to take care of. Everything else was great.
Reviewed on 23 Oct 2025
Red Roof Inn Winchester, VA
Good stay for an overnight trip. Kumar treated us like very special people! Clean and very comfortable. Only problem - ADA shower very difficult to use for someone less then 5’4. Reaching the shower head was impossible. Would not recommend this place for special needs.
Reviewed on 22 Oct 2025
Comfort Inn & Suites Winchester
Clean rooms and comfortable beds and bedding. Plentiful bath towels. Convenient location
Reviewed on 24 Oct 2025
Hampton Inn Winchester-University/Mall Area
Parking area felt very safe. Fruit available for breakfast.
Reviewed on 21 Oct 2025
Microtel Inn & Suites by Wyndham Winchester
The afternoon and evening staff, particularly the girl at check in later in the day, were lovely and professional. They completed their duties pleasantly and in a respectful manner. They provided detailed answers and ensured our comfort. The morning staff, less than stellar. Out of uniform, conversational ...
Reviewed on 21 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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