Old Town Winchester Travel Guide
Tourist Guide
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 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.
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.
Our pick of the best Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
I was very pleased with the accommodations at this hotel. I can't stress enough how incredible the pool is. The hot tub is great too, but I was impressed with the pool and would visit again just for that. Make sure to check that out!
Reviewed on 31 Oct 2025
Travelodge by Wyndham Winchester
Such a great find for our overnight Stay and last minute with excellent price. Comfortable bed and fantastic staff. Breakfast lacking but expected.
Reviewed on 6 Nov 2025
La Quinta Inn & Suites by Wyndham Winchester
Clean room
Reviewed on 8 Nov 2025
Comfort Inn & Suites Winchester
It was the cleanest and most friendly place I’ve ever stayed at.The breakfast was amazing the beds were very comfortable hardly any noise just a great place to stay.
Reviewed on 5 Nov 2025
Microtel Inn & Suites by Wyndham Winchester
Excellent accommodations
Reviewed on 7 Nov 2025
Country Inn & Suites by Radisson, Winchester, VA
Breakfast great, heating fine
Reviewed on 5 Nov 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.
