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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 5,715 reviews and posted 1,459 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
My girlfriend and I decided to stay at this hotel while spending a few days traveling on Skyline Drive and taking in the fall colors. We had not made any hotel reservation and...
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The George Washington Hotel
#2 Hotel in Winchester
The George Washington Hotel
We booked one night, but liked it so much that we cancelled a reservation at another hotel and came back. The staff at the check in desk were very courteous and welcoming. The...
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Holiday Inn Winchester Southeast-Historic Gateway
#3 Hotel in Winchester
Holiday Inn Winchester Southeast-Historic Gateway
My wife and I stayed at the Holiday Inn in Winchester for one night on the 18th of October. The facility is very modern, clean, and welcoming. Our room was clean and the overall...
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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.