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 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
I love this hotel. I have stayed here once or twice a year over the past few years for the affordability, cleanliness, pool, hot tub, and location on my way up north. This past stay I noticed they are doing their best to keep up with increasing maintenance demands and decreasing profits.
Reviewed on 29 Dec 2025
La Quinta Inn & Suites by Wyndham Winchester
Everything was great
Reviewed on 28 Dec 2025
Microtel Inn & Suites by Wyndham Winchester
Great staff. Clean room. Excellent location
Reviewed on 26 Dec 2025
Travelodge by Wyndham Winchester
All of the above mentioned and a great, nutritious and varied breakfast. Also, both regular and decaf coffee were available in the breakfast area whenever I wanted it. Lastly, plentiful parking.
Reviewed on 27 Dec 2025
Days Inn by Wyndham Charles Town/Harpers Ferry
The room is clean. The staff is friendly. The breakfast was good. No-frills hotel, but clean and efficient.
Reviewed on 13 Dec 2025
Comfort Inn & Suites Winchester
The facilities were very clean. Location was great. Staff was super helpful and nice. My only issue: Curtains! Our room faced the parking lot in front of the hotel. The lot is very well lit, which is much appreciated, but the heavy curtains in our room could not be drawn together. The light one do, ...
Reviewed on 29 Dec 2025
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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.
