Old Town Winchester Travel Guide
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.
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
Toilets are low
Reviewed on 7 May 2026
Spark by Hilton Winchester
Clean, comfortable room. Friendly, helpful staff. Good continental breakfast and coffee. Easy parking, location close to restaurants and shops but set apart enough that one doesn’t hear much noise coming from outside their hotel room.
Reviewed on 7 May 2026
Travelodge by Wyndham Winchester
Clean and comfortable. Good for the price.
Reviewed on 6 May 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Perfect hotel. I love this hotel.
Reviewed on 5 May 2026
Microtel Inn & Suites by Wyndham Winchester
Quiet. Very nice front desk lady gave us extra blankets when we asked. Great breakfast!
Reviewed on 6 May 2026
La Quinta Inn & Suites by Wyndham Winchester
Quiet clean room. Had dog with me. staff was very kind about his barking. They have a special floor for dogs.
Reviewed on 5 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.
