Winchester Historic District Holidays

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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

103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
AU$193
7 Sept - 8 Sept
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel
Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city

Winchester VA
AU$464
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (18 reviews)
"Perfect location for exploring Winchester. Beautiful rooms. Clean and comfortable."

Reviewed on 27 July 2026

Nostalgia Lane in the heart of the city
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA
Fully refundable
AU$158
27 Sept - 28 Sept
includes taxes & fees
Holiday Inn Winchester Se-Historic Gateway by IHG
See all 377 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays
family friendly holidays
Family Friendly Holidays
Family Friendly Holidays
golf holidays
Golf Holidays
Golf Holidays
luxury holidays
Luxury Holidays
Luxury Holidays
romantic holidays
Romantic Holidays
Romantic Holidays
ski holidays
Ski Holidays
Ski Holidays
honeymoon holidays
Honeymoon Holidays
Honeymoon Holidays
pet friendly holidays
Pet-friendly Holidays
Pet-friendly Holidays
Spa Holidays
Spa Holidays
Spa Holidays

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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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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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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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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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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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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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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.