Winchester Historic District Vacations
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Winchester Historic District Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
₩169,708
₩192,280 total
Aug 27 - Aug 28
includes taxes & fees
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
₩111,870
₩126,749 total
Sep 17 - Sep 18
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"Very clean and lovely. We enjoyed it"
Reviewed on Aug 20, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
₩129,177
₩147,942 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (1,017 reviews)
"Room was clean, roomy and comfy. Comfy chair with ottoman was a plus. Air conditioner was noisy. Breakfast is what you get at other hotels for free. $15 here. Bench out front really needs to be cleaned. Covered with bird poop. Friendly and helpful staff"
Reviewed on Aug 20, 2026
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.
Stay near popular Winchester Historic District attractions
Shenandoah Valley Discovery Museum
8.6/10 (78 reviews)
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants.
Winchester Little Theater
7.6/10 (37 reviews)
Enjoy a show at Winchester Little Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
Bright Box Theater
7.8/10 (18 reviews)
Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
Stonewall Jackson's Headquarters
10.0/10 (1 review)
Learn about the local history of Winchester when you take a trip to Stonewall Jackson's Headquarters. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Handley Regional Library
9.6/10 (4 reviews)
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
George Washington's Office
8.0/10 (1 review)
You can learn about the history of Winchester when you stop by George Washington's Office. While in this walkable area, you can savor the top-notch restaurants.
Old Court House Civil War Museum
8.0/10 (1 review)
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 savor the top-notch restaurants.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.