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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 7,250 reviews and posted 2,261 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
Not only is this hotel excellent in all the qualities a traveler wants, but the attentive, friendly and most professional staff makes sure your stay is restful and without worry...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
My husband and I chose The George Washington Hotel as a special spot to celebrate his birthday on our way to the Outer Banks. We were grateful to get a room on short notice...
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Hampton Inn Winchester-North
#3 Hotel in Winchester
Hampton Inn Winchester-North
Hampton Inn is a budget, limited service product of Hilton. As the saying goes, what could possibly go wrong? However, in this case, the experience was flawless, from breakfast...
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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.