
Old Town Winchester Holidays
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Top hotels in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is 3.108.054 ₫ per night from 1 Sept to 2 Sept
3.108.054 ₫
3.521.424 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
Super Getaway
"Great old hotel. Quiet, comfortable, beautiful. Staff were wonderful. Perfect location for walking around the downtown mall."
Reviewed on 23 Aug 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 2.698.996 ₫ per night from 1 Sept to 2 Sept
2.698.996 ₫
2.936.539 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,136 reviews)
"The bedroom was clean. Some area a bit older looking but good. Hall ways a little smelly like needs carpets refreshed. But not all that bad.."
Reviewed on 25 Aug 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is 2.161.356 ₫ per night from 7 Sept to 8 Sept
2.161.356 ₫
2.430.735 ₫ total
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Clean and staff was great."
Reviewed on 23 Aug 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.
Frequently asked questions
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 top-notch restaurants or cosy cafes 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.