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New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

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 9,610 reviews and posted 3,206 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
A wonderful place, with all the amenities and very clean. Friendly staff and facilities overall are great. They let me check out a little later, and even provided a free water...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
We knew the first time we walked into the marbled and well appointed lobby of this grand old beauty that we were in for a special experience. We really enjoyed the old pictures...
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Hampton Inn Winchester-University/Mall Area
#3 Hotel in Winchester
Hampton Inn Winchester-University/Mall Area
Lack of attention by both desk clerks at check-in. The clerk actually checking me in paid more attention to what was going on with the computer. Did not say "welcome" or any...
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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.