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 3.431.471 ₫ per night from 11 Jun to 12 Jun
3.431.471 ₫
3.887.857 ₫ total
11 Jun - 12 Jun
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"It may have been the number one hotel in town 30 years ago. Today, however, the balance between price and quality has shifted heavily toward the price, while the quality has unfortunately fallen behind. We stayed in a suite directly under the roof, and throughout our entire stay there was a loud ..."
Reviewed on 31 May 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is 2.460.558 ₫ per night from 30 Jun to 1 Jul
2.460.558 ₫
2.787.812 ₫ total
30 Jun - 1 Jul
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Staff was very nice"
Reviewed on 2 Jun 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is 2.999.840 ₫ per night from 29 Jun to 30 Jun
2.999.840 ₫
3.263.827 ₫ total
29 Jun - 30 Jun
includes taxes & fees
9/10 Wonderful! (902 reviews)
"Amazing hotel, allowed me to check in early. Very nice and clean rooms"
Reviewed on 3 Jun 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.
Popular places to visit
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 cosy cafes or top-notch restaurants in this walkable area.
Jim Barnett Park
Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.