Winchester Historic District Holidays
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Price found within the past 48 hours. Click for updated prices.
Rachael's Inner Harbor Boutique Inn
Ridgely's Delight
S$1,130
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
8.8/10 Excellent! (11 reviews)
We had a great time. Was in town for a baseball game and the location was great. The room was clean and very large. We will most likely be back next time the PHILLIES are in town.
Reviewed on 11 Aug, 2026
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Fells Point
S$1,075
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
9.2/10 Wonderful! (835 reviews)
The evening I checked in, your front desk man: Eric was friendly and extremely helpful. The room was spotless and the beds were amazingly comfortable. I will recommend this hotel to friends and family. 2 thumbs up, get adventurous fun!
Reviewed on 13 Aug, 2026
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
S$177
23 Aug - 24 Aug
includes taxes & fees
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
S$112
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"The person working at reception on Saturday, August 15 (from midday through evening) was so helpful and nice. She deserves a raise or promotion if she wants it!"
Reviewed on 17 Aug, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
S$136
23 Aug - 24 Aug
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"All good!"
Reviewed on 16 Aug, 2026
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
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.
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.
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.
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.
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.
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.
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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