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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 5,652 reviews and posted 1,450 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
Hotel overall is in a very good state, makes you like to be there. Service was very friendly. Breakfast was great, with hot offers and various cereals, fresh fruit, fresh...
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The George Washington Hotel
#2 Hotel in Winchester
The George Washington Hotel
We stayed on a Saturday night during a friends wedding along with several other attendees. Being familiar with the building we were thoroughly impressed with the renovation and...
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Holiday Inn Winchester Southeast-Historic Gateway
#3 Hotel in Winchester
Holiday Inn Winchester Southeast-Historic Gateway
Clean hotel. Lobby in good condition. Friendly and helpful reception. Has a bar and restaurant on premise and other dining options about 500 meters away. Room was clean 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.