Winchester Historic District Holidays from NZ$2,725

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Top Holiday Package Deals in Winchester Historic District

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Annapolis
Graduate by Hilton Annapolis
Sandaway Suites & Beach
Historic Inns of Annapolis
134 Prince - Luxury Boutique Hotel

Our pick of the best Winchester Historic District Hotel Deals

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is NZ$241 per night from 17 Aug to 18 Aug
NZ$241
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"This hotel is great. I’ve stayed there before and we’ll stay there again. My only gripe is that the hot tub wasn’t hot…it was warm, and there were no jets of any consequence… I absolutely recommend this hotel!"

Reviewed on 6 Aug. 2025

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is NZ$189 per night from 1 Sept to 2 Sept
NZ$189
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,123 reviews)
"One of our fave places to stay when we visit Winchester."

Reviewed on 10 Aug. 2025

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is NZ$175 per night from 24 Aug to 25 Aug
NZ$175
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Wish breakfast was free. Other than that is was good."

Reviewed on 6 Aug. 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.