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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 6,340 reviews and posted 1,675 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
Worth the money. Staff excellent, helpful. Rooms clean. Bathrooms clean. Accommodating to our Labradors. Only negative is some guests not picking up their pets poops. I would stay...
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The George Washington Hotel
#2 Hotel in Winchester
The George Washington Hotel
I have stayed here many times and always find the rooms to be very comfortable and reasonably priced. The service at the Dancing Goat can be variable, especially at breakfast...
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Holiday Inn Winchester Southeast-Historic Gateway
#3 Hotel in Winchester
Holiday Inn Winchester Southeast-Historic Gateway
I enjoyed my stay. Comfortable rooms and good staff. Good location to restaurants and a grocery store. My suggestion is that the fitness center needs to be expanded with more...
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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.