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.
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.
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.
Activities
Shenandoah Tour: Self-Guided Drive
Our pick of the best Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
The hotel is in a great location in town, and in the region. My only negative comment is the charge to use the hotel parking lot. A little ridiculous in my opinion.
Reviewed on 10 May 2026
Spark by Hilton Winchester
Room was large with comfortable beds.
Reviewed on 10 May 2026
Travelodge by Wyndham Winchester
Air conditioning and heat worked properly, and easy to use. I like that the door to room has an alarm if door is left open. I love the big parking lot and design. Great for semi's, RV's, etc. Staff was so friendly and helpful at daytime front desk. I love the pull-down shades verses curtains. It ...
Reviewed on 8 May 2026
Microtel Inn & Suites by Wyndham Winchester
This was my first stay at a Microtel and i was very impressed wirh the design and how well sound was controlled. I'll definitely stay again.
Reviewed on 10 May 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
No free breakfast.
Reviewed on 9 May 2026
La Quinta Inn & Suites by Wyndham Winchester
Bed was extremely comfortable. Linens were clean and of good quality. Breakfast area was clean, well stocked and attended to. Only one staff member during weekend evening but worked hard to satisfy my issue with non-working remote. Should have been spare or extra remotes at front desk. Hall carpeting ...
Reviewed on 10 May 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.
