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Your Winchester Vacation
The rich history and small-town feel are just the start of the things Winchester has on offer. Experience the best of this city your way with a tailor-made Winchester vacation package. You'll want to do some exploring during your trip to Winchester. Find time for big-name attractions such as Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Winchester vacation is easy with Expedia.
The Latest Winchester vacation packages

DoubleTree by Hilton Hotel Laurel
Reviewed on Oct 3, 2025

InterContinental Washington D.C. - The Wharf by IHG
Reviewed on Oct 2, 2025

Graduate by Hilton Annapolis
Reviewed on Oct 3, 2025

Pier 5 Hotel Baltimore
Reviewed on Oct 1, 2025

Historic Inns of Annapolis
Reviewed on Oct 3, 2025
Discover the most popular places to visit in Winchester

Museum of the Shenandoah Valley
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.

Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Winchester Medical Center
Though Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here.
Winchester Hotel Deals

Hampton Inn Winchester-University/Mall Area
Reviewed on Oct 3, 2025

La Quinta Inn & Suites by Wyndham Winchester
Reviewed on Oct 1, 2025

Travelodge by Wyndham Winchester
Reviewed on Sep 27, 2025
Winchester Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Population | 27,300 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
Top Sights | Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theater |
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