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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 10,401 reviews and posted 3,625 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
Staff was courteous, respectful and knowledgeable. Rooms were clean, provided ample room and the beds were very comfortable. Free breakfast and internet were great. The value...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
Our group of ladies had a wonderful weekend celebrating my birthday. After arriving to Winchester from Dulles the front desk allowed us to check in early. Taryn always greets you...
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Hampton Inn Winchester-University/Mall Area
#3 Hotel in Winchester
Hampton Inn Winchester-University/Mall Area
The staff here was A 1 and they were extremely helpful & pleasant! The only problem we had was with the mattress being too soft. Breakfast was excellent. All in all, we would stay...
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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.