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 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.
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
Microtel Inn & Suites by Wyndham Winchester
Very clean property, room. Staff was very friendly. Breakfast wasn’t continental but a big breakfast, complete! Pancakes, eggs, sausage cereal, pastries, fruit! Well worth the price.
Reviewed on 16 Apr 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Very clean & functional room. Bed too soft and lLOUD thrumming noise all night long prevented sufficient sleep.
Reviewed on 13 Apr 2026
La Quinta Inn & Suites by Wyndham Winchester
The breakfast was the worst I have EVER had! The “scrambled eggs” were not real. They were egg beaters—- horrible, dry, tasteless. The “biscuits were even worse. They were the consistency of compressed sawdust and tasted worse! The hard boiled eggs had GREY yolks! One bite and I was horrified. Breakfast ...
Reviewed on 19 Apr 2026
Sleep Inn & Suites Winchester near University
This property has been on a steady decline. 1st floor ice maker has been "out of order" for over a year now. Remote power button didn't work, toilet seat shifted, chair in the room was leaning to one side as if it could break at any wrong move. Children had stayed in this room, and Stickers were ...
Reviewed on 18 Apr 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Found this hotel a couple of years ago and it is now our goto hotel on our way to Myrtle Beach .... great restaurant with upbeat fun staff ... for dinner and for breakfast .... the rooms are more than adequate after driving for 9 hours ... clean and very comfortable beds ......
Reviewed on 14 Apr 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.
