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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 9,809 reviews and posted 3,326 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
“Good stay” 09/29/2016
Country Inn & Suites is always our hotel of choice. We enjoy the hot breakfasts and quality that we expect from these hotels. We only stayed one night on our way to our final...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
“Very nice!” 09/29/2016
Last stop before we headed back home from a road trip. The bed was very comfortable and the linens were nice and plush. The pool was really neat and I enjoyed it and the hot tub...
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Hampton Inn Winchester-University/Mall Area
#3 Hotel in Winchester
Hampton Inn Winchester-University/Mall Area
Really enjoyed my stay, it's a great location and I received wonderful service!!! I'd stay again!!! Clean rooms, great breakfast wonderful staff. Thanks for making my trip so...
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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.