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
3.372.409 ₫
3.820.939 ₫ total
28 Oct - 29 Oct
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"rooms are clean, spacious, and serviced everyday. Good breakfast on offer and the Bar is good too. Greal location and good parking. Staff very helpful and knowledgeable about the area. Shenandoah mountains are wonderful. Lots of wineries and farmers market near by"
Reviewed on 21 Oct 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
2.152.051 ₫
2.395.233 ₫ total
22 Nov - 23 Nov
includes taxes & fees
9.2/10 Wonderful! (1,447 reviews)
"I was not able to get a first floor room, and the hostess in the morning was terribly rude."
Reviewed on 21 Oct 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
1.956.763 ₫
2.177.878 ₫ total
22 Nov - 23 Nov
includes taxes & fees
8.2/10 Very good! (1,011 reviews)
"The price is right, the breakfast is ok, the laundry required quarters, and getting quarters was a challenge"
Reviewed on 20 Oct 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 savour the top-notch restaurants.
Bright Box Theater
7.8/10 (18 reviews)
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
9.6/10 (4 reviews)
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.
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 savour the top-notch restaurants.
Stonewall Jackson's Headquarters
10.0/10 (1 review)
Find out about the history of Winchester when you take a trip to Stonewall Jackson's Headquarters. Visit the cosy cafes or top-notch restaurants in this walkable area.
Winchester Little Theater
7.6/10 (37 reviews)
Enjoy a show at Winchester Little Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.
George Washington's Office
8.0/10 (1 review)
You can find out about the history of Winchester with a visit to George Washington's Office. While in this walkable area, you can savour the top-notch restaurants.