
Winchester Historic District Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Winchester Historic District

The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is 3.329.882 ₫ per night from 28 Aug to 29 Aug
3.329.882 ₫
3.772.756 ₫ total
28 Aug - 29 Aug
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Great location for dining and shopping. Walkable and safe. Very historic hotel with great ambiance and architecture."
Reviewed on 17 Aug 2025

La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is 2.697.559 ₫ per night from 2 Sept to 3 Sept
2.697.559 ₫
2.934.976 ₫ total
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (2,133 reviews)
"Just a suggestion. I am disabled and was placed in a lovely room on the 6th floor. The fire alarm went off and my concern is how is someone in a wheelchair going to evacuate without the elevator. Maybe all ada rooms shou"
Reviewed on 19 Aug 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is 2.155.944 ₫ per night from 24 Aug to 25 Aug
2.155.944 ₫
2.424.648 ₫ total
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Bed comfort"
Reviewed on 12 Aug 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit

Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.

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.
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.