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 top-notch restaurants or cosy cafes in this walkable area.
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.
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.
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.
George Washington's Office
You can find out about the history of Winchester with a visit to George Washington's Office. While in this walkable area, you can savour the top-notch restaurants.
Top hotels in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel
"This place was perfect! Close to old town, clean, helpful, we were so pleased with our stay!"
Reviewed on 18 Jun 2026

Spark by Hilton Winchester
"Quick & easy."
Reviewed on 19 Jun 2026

TRU By Hilton Winchester
"Five stars throughout the hotel ,nice place"
Reviewed on 20 Jun 2026

Travelodge by Wyndham Winchester
"First room smelled like cigarette smoke. They were accommodating about getting us new room."
Reviewed on 20 Jun 2026

Ramada by Wyndham Strasburg/Shenandoah Valley
"Kris was very accommodating at check in! Thank you!"
Reviewed on 20 Jun 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
"Staff were polite and helpful, room was clean."
Reviewed on 14 Jun 2026
Where to stay in Old Town Winchester

Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.




