Old Town Winchester Travel Guide
Tourist Guide
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 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.
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.
Our pick of the best Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
Clean nice room Great location for restaurants
Reviewed on 28 Jan 2026
La Quinta Inn & Suites by Wyndham Winchester
Clean, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience.
Reviewed on 31 Jan 2026
Travelodge by Wyndham Winchester
Room was good for the price, staff was friendly and helpful
Reviewed on 4 Feb 2026
Microtel Inn & Suites by Wyndham Winchester
Room was very clean and spacious, staff was wonderful!
Reviewed on 31 Jan 2026
Quality Inn Winchester
The staff (phenomenal), the cleanliness, the attention to detail! The lady overseeing breakfast was a machine. Everything tidied up and perfect. The front desk staff were amazing!! Best staff we've ever seen and we travel a LOT!! 100% recommend staying here. It was less than a mile from the concert ...
Reviewed on 18 Jan 2026
TownePlace Suites by Marriott Front Royal
Clean room, friendly and helpful staff, good breakfast, I would stay again.
Reviewed on 16 Jan 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.
