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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 6,242 reviews and posted 1,613 candid photos for Winchester hotels. Book your Winchester vacation today!
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Country Inn & Suites Winchester
#1 Hotel in Winchester
Country Inn & Suites Winchester
We stopped while travelling from florida to NY. It was a snow storm. The hotel was fully booked. It was a great stop. The rooms were clean, the pool was great for the kids. The...
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The George Washington Hotel
#2 Hotel in Winchester
The George Washington Hotel
We arrived yesterday from Gettysburg, PA, for a quick 2 day mini vacation. The hotel is lovely and the staff is extremely friendly and helpful. We reserved a deluxe king room, but...
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Holiday Inn Winchester Southeast-Historic Gateway
#3 Hotel in Winchester
Holiday Inn Winchester Southeast-Historic Gateway
Customer service is exceptional and the price is reasonable. They have an excellent business center, a reliable internet, well equipped exercise room, and an indoor swimming...
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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.