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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 6,686 reviews and posted 1,747 candid photos for Winchester hotels. Book your Winchester vacation today!
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Country Inn & Suites By Carlson, Winchester, VA
#1 Hotel in Winchester
Country Inn & Suites By Carlson, Winchester, VA
Clean and comfortable with reasonable pricing and decent breakfast. I'd stay here again! That said, Embassy Suites typically has the best breakfasts. But this was a good hotel...
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The George Washington Hotel
#2 Hotel in Winchester
The George Washington Hotel
This Hotel is extremely Nice! They have Great rooms; reasonable prices; good quality and clean. Nice restaurant and bar on location; musicians on the weekends. Pool and Spa...
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Hampton Inn Winchester-North
#3 Hotel in Winchester
Hampton Inn Winchester-North
We were there with a large group and recieved a discounted rate. there was some building repairs underway while we were there but it was not an issue. The pool was empty and...
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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.