Old Town Winchester
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. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Museum of the Shenandoah Valley
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses 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 savor the top-notch restaurants.
Bright Box Theater
Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor 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 savor the top-notch restaurants.
George Washington's Office
You can learn about the history of Winchester when you stop by George Washington's Office. While in this walkable area, you can savor the top-notch restaurants.
Things to do
Shenandoah Tour: Self-Guided Drive
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
Clean rooms, nice water pressure and never ending hot water ! Only improvements I would suggest is for holiday stays like new years that has a bar maybe make it for adults who want to enjoy the music and not filled with kids and those boys t
Reviewed on Jan 2, 2026
Microtel Inn & Suites by Wyndham Winchester
Yep everything was good
Reviewed on Jan 3, 2026
La Quinta Inn & Suites by Wyndham Winchester
Clean room, nice layout with sink separate from shower/toilet area. Lived the soft reading lights by the bed.
Reviewed on Jan 3, 2026
Travelodge by Wyndham Winchester
No need for Air conditioning, parking great
Reviewed on Jan 4, 2026
Comfort Inn & Suites Winchester
We stayed twice,one night 2 weeks apart.The rooms on the parking lot side have a lot less outdoor noise, the rooms on the back of the building are against Interstate 81. We got very little sleep in the room against the highway because of constant noise from traffic. Always ask for an odd number room ...
Reviewed on Jan 3, 2026
Quality Inn Winchester
Clean room, front dest service.
Reviewed on Jan 5, 2026
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 Shenandoah Valley Discovery Museum.
