Winchester Historic District Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Tina McClelland
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 3.337.228 ₫ per night from 15 Dec to 16 Dec
3.337.228 ₫
3.781.080 ₫ total
15 Dec - 16 Dec
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
Comfortable room with a great, roomy shower with good water pressure. Saturday night live music in the bar was a lively treat!
Reviewed on 16 Nov 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is 1.844.500 ₫ per night from 19 Nov to 20 Nov
1.844.500 ₫
2.006.816 ₫ total
19 Nov - 20 Nov
includes taxes & fees
8.4/10 Very Good! (1,086 reviews)
Absolutely great stay. Nothing needed was lacking. Room was spotless and comfortable. Staff were so pleasant. Appreciate everything about this hotel.
Reviewed on 16 Nov 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
Fully refundableReserve now, pay when you stay
The price is 2.576.006 ₫ per night from 1 Dec to 2 Dec
2.576.006 ₫
2.802.642 ₫ total
1 Dec - 2 Dec
includes taxes & fees
9.2/10 Wonderful! (2,216 reviews)
A run of the mill motel good for a travel break.
Reviewed on 16 Nov 2025
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
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.
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 top-notch restaurants or cosy cafes in this walkable area.
Old Court House Civil War Museum
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.