Winchester Historic District Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 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
Our pick of the best 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
The price is NZ$244 per night from 26 July to 27 July
NZ$244
26 July - 27 July
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Cool historic hotel! Very clean and nice!"
Reviewed on 1 July 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is NZ$164 per night from 29 July to 30 July
NZ$164
29 July - 30 July
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."
Reviewed on 28 June 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is NZ$179 per night from 26 July to 27 July
NZ$179
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Great stay, very helpful staff during our late arrival"
Reviewed on 1 July 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.