Winchester Historic District Vacations from ￥394,688
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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
The Latest Winchester Historic District Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Lyle Washington D.C.
Northwest
￥431,064
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Baltimore (BWI)
9.4/10 Exceptional! (1,645 reviews)
Bed comfortable. Brighter room than most nearby hotels. Restaurant very good but very noisy while we were there. Young people seem to be the dominant group.
Reviewed on Oct 9, 2026
Winchester Historic District Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
￥20,587
￥23,325 total
Oct 28 - Oct 29
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"The staff was just not welcoming or helpful."
Reviewed on Oct 7, 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
￥13,678
￥15,223 total
Nov 8 - Nov 9
includes taxes & fees
9.2/10 Wonderful! (1,436 reviews)
"Very clean room. Well-lit parking lot."
Reviewed on Oct 8, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
￥13,466
￥14,988 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Everything was good"
Reviewed on Oct 9, 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.
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.
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.
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.
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.
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.