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 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.
Our pick of the best Old Town Winchester Hotel Deals
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
Breakfast menu was simple but fresh.
Reviewed on 16 May 2026
Travelodge by Wyndham Winchester
The room was clean, and the staff was very welcoming and friendly. The location is especially convenient for truckers or anyone needing a quick overnight stop. The rooms have been partially updated with new flooring and a more modern look, but the walls still need some attention, which made the updates ...
Reviewed on 16 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
You have to pay 8.00 for breakfast, but it was very good. Room was clean, safe location.
Reviewed on 16 May 2026
La Quinta Inn & Suites by Wyndham Winchester
Be Aware!! Parking was a bit hard( we were pulling an enclosed trailer) had to back out from around the building because it did not circle all the way around . Room was clean and comfortable bed was soft, breakfast was the usually continental hot breakfast nothing special but ok. Would stay ...
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.
