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.
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
The staff was helpful and kind. The architecture was incredible.
Reviewed on 12 May 2026
Spark by Hilton Winchester
Could have had more of a selection for breakfast. Christine welcomed me with a smile & welcome. Makes you feel good right off the bat!
Reviewed on 15 May 2026
Travelodge by Wyndham Winchester
Location was convenient. Staff were freindly and helpful.
Reviewed on 15 May 2026
Microtel Inn & Suites by Wyndham Winchester
The hotel was clean and the bed was comfortable. However, there were no cups in the room for coffee, yet there was a coffee machine and lids for cups. I called down to the front desk and was told they don't supply cups in the room and if I wanted a cup I had to go down to the coffee bar to get one. ...
Reviewed on 13 May 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
It's a great hotel with friendly staff. Made our travel alot easier
Reviewed on 15 May 2026
La Quinta Inn & Suites by Wyndham Winchester
Friendly staff, clean spacious rooms, plenty of parking and a great breakfast. We enjoyed our stay here for sure!!
Reviewed on 15 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.
