Winchester Historic District Holidays

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Top hotels in Winchester Historic District

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA
€130
4 Oct - 5 Oct
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"The room was very comfortable. Uno's was a wonderful place to eat!"

Reviewed on 27 Sept 2026

The George Washington Hotel, A Wyndham Grand Hotel
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
€67
28 Sept - 29 Sept
includes taxes & fees
Travelodge by Wyndham Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
€95
4 Oct - 5 Oct
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Overnight stay on a road trip. Wonderful front desk staff, friendly & professional. Room was in excellent condition. Very comfy bed, clean bathroom with great towels, delicious breakfast buffet with plenty of options. Definitely on the list to stay again!"

Reviewed on 25 Sept 2026

TRU By Hilton Winchester
See all 388 properties in Winchester Historic District
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

Shenandoah Valley Discovery Museum

8.6/10 (78 reviews)
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.
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Bright Box Theater

7.8/10 (18 reviews)
Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.
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Stonewall Jackson's Headquarters

10.0/10 (1 review)
Find out about the history of Winchester when you take a trip to Stonewall Jackson's Headquarters. Visit the cosy cafes or top-notch restaurants in this walkable area.
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Old Court House Civil War Museum

8.0/10 (1 review)
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.
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Handley Regional Library

9.6/10 (4 reviews)
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.
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Winchester Little Theater

7.6/10 (37 reviews)
Enjoy a show at Winchester Little Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.
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George Washington's Office

8.0/10 (1 review)
You can find out about the history of Winchester with a visit to George Washington's Office. While in this walkable area, you can savour the top-notch restaurants.
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