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Winchester Vacation Packages

Stonewall Jackson Headquarters Museum
Old Town WInchester
A really cool old house across from the library.
Winchester Vacation Packages
Want to book a vacation to Winchester? Whether you're off for a romantic vacation, family trip, or an all-inclusive holiday, Winchester vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Winchester on TripAdvisor by comparing Winchester hotel and flight prices. Travelers like you have written 10,518 reviews and posted 3,718 candid photos for Winchester hotels. Book your Winchester vacation today!
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Country Inn & Suites By Carlson, Winchester
#1 Hotel in Winchester
Country Inn & Suites By Carlson, Winchester
This Country Inn and Suites is a favorite of mine. Always hospitable and clean. Located near everything! The Alamo Drafthouse movie theater is in the same parking lot and great...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
We recently spent a Sunday night at the GW Hotel. Great old place that has been meticulously renovated. Check in was a snap, parking was a bit of a hassle - definitely go with the...
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Hampton Inn Winchester-University/Mall Area
#3 Hotel in Winchester
Hampton Inn Winchester-University/Mall Area
Excellent value and comfortable, great location, easy access to highway. Right across from Shaeandoah University, breakfast is complemtery and flavorable. Coffee is always...
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Cheap Flights to Winchester
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†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.