Winchester Historic District Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Winchester Historic District
Price found within the past 48 hours. Click for updated prices.
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
CA $169
CA $192 total
Sep 7 - Sep 8
includes taxes & fees
Nostalgia Lane in the heart of the city
Winchester VA
CA $256
CA $465 total
Sep 2 - Sep 3
includes taxes & fees
9.2/10 Wonderful! (18 reviews)
"Perfect location for exploring Winchester. Beautiful rooms. Clean and comfortable."
Reviewed on Jul 27, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
CA $107
CA $122 total
Sep 28 - Sep 29
includes taxes & fees
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.
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.
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.
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.
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.