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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 6,575 reviews and posted 1,706 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
Very good value for the price. Easy to find off the interstate. Staff were polite and professional. Room was quiet. You will find this place a good place to overnight. Their...
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The George Washington Hotel
#2 Hotel in Winchester
The George Washington Hotel
We stopped here for one night when travelling to Washington, DC, and were very happy with our choice. Our room was very spacious with a King-size bed, a table for working at, a...
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Hampton Inn Winchester-North
#3 Hotel in Winchester
Hampton Inn Winchester-North
The hotel was all that we expected, clean quite room. Was pleasantly surprised by the whirlpool tub for 2. The staff was exceptional in their attentiveness. It was a very...
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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.