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 cosy cafes or top-notch restaurants in this walkable area.
Jim Barnett Park
Explore the great outdoors at Jim Barnett Park, a lovely green space in 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.
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.
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.
Things to do
Shenandoah Tour: Self-Guided Drive
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
"Great old hotel located in the downtown neighborhood. Room was large with a great bathroom. This is always our first choice when visiting Winchester"
Reviewed on 28 May, 2026
Spark by Hilton Winchester
"Clean room, friendly staff. A light breakfast that wasn't anything really special. Traffic in the area around the hotel can be intense, especially if you need to make a left turn on S. Pleasant Valley Road on the way out."
Reviewed on 29 May, 2026
TRU By Hilton Winchester
"The rooms here have a bright, cheerful look, very clean, comfy beds, hot shower, lots of pillows. Love the large TV screen. There was a long padded bench to hold more than two suitcases!! All the bathroom toiletries are pump bottles, very hygienic. There were many hooks for clothes in the bathroom ..."
Reviewed on 30 May, 2026
Microtel Inn & Suites by Wyndham Winchester
"Breakfast was burnt fried eggs and wet ham slices. Stale bread and bagels"
Reviewed on 29 May, 2026
Travelodge by Wyndham Winchester
"Nice place to sleep, clean rooms and big parking space."
Reviewed on 26 May, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
"Very clean and pleasant room. Staff was very helpful. Would definitely stay here again."
Reviewed on 29 May, 2026
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.
