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 top-notch restaurants or cosy cafes in this walkable area.
Jim Barnett Park
Explore the great outdoors at Jim Barnett Park, a lovely green space in 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.
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.
Things to do
Shenandoah Tour: Self-Guided Drive
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
Beautiful hotel. They just need to bring the price down a little.
Reviewed on 26 Apr 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Good for an overnight stay on our way up north.
Reviewed on 20 Apr 2026
Microtel Inn & Suites by Wyndham Winchester
Facility is always clean and staff is great
Reviewed on 26 Apr 2026
La Quinta Inn & Suites by Wyndham Winchester
Hotel was clean, staff were attentive and breakfast was good.
Reviewed on 25 Apr 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
I accidentally booked a handicapped accessible room and ended up with two double beds instead of queens which was unfortunate, but my fault. However, the room was not in good shape, plus the beds would squeak every time you moved. In addition, there was a bright light outside our window, which shined ...
Reviewed on 26 Apr 2026
Travelodge by Wyndham Winchester
Parking was close and well lit
Reviewed on 17 Apr 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.
