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 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 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 top-notch restaurants or cosy cafes in this walkable area.
Our pick of the best Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
This is a great renaissance hotel. The renovation of the interior is magnificent. The staff is very professional, competent and accommodating. Notables are the lobby including the bar and the pool spa. Best hotel shower head ever! The dining options in walking distance are fantastic. Definite return ...
Reviewed on 31 Mar 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Breakfast was excellent and all the staff were very friendly.
Reviewed on 30 Mar 2026
La Quinta Inn & Suites by Wyndham Winchester
The breakfast was subpar. Food was sparse Waffle maker didn't consistently work.
Reviewed on 1 Apr 2026
Sleep Inn & Suites Winchester near University
I only stayed for about an hour. The room was freezing cold as it was dead of winter and freezing out. There was no heat turned on in the room when I got there so it was quite a while before the room actually reached a tolerable temperature
Reviewed on 26 Mar 2026
Microtel Inn & Suites by Wyndham Winchester
Being greeted by an alert and cheerful front desk person when checking in at 1 am set the tone for feeling comfortable about how the rest of the stay was going to go. i'll definitely try other Microtel Inn & Suites by Wyndham on my next trip.
Reviewed on 29 Mar 2026
Hampton Inn Winchester-University/Mall Area
Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel
Reviewed on 15 Mar 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.
