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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 8,344 reviews and posted 2,486 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
Everything was provided for the comforts of home and then some. The pool was heated to a very comfortable temp. Pool and hot tub were clean. Staff was extremely courteous and...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
Found this on a whim. My husband and I have been back just for the hotel 6 times! Beautiful elegant restored historic building. Close to restaurants, pubs, boutique shops and...
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Hampton Inn Winchester-North
#3 Hotel in Winchester
Hampton Inn Winchester-North
We stayed at this hotel on our way down south on January 30, 2016. First impressions are important and the man at the front desk (Tom?) was courteous, helpful and generally left...
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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.