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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 7,486 reviews and posted 2,403 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
We stayed here for 2 nights while visiting family in the area. It's a very well maintained, clean, nice property. We made extensive use of the very nice pool area. The breakfast...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
This hotel is only a few blocks from the pedestrian walk on Loudon Street, which has great restaurants and shopping. We didn't eat at the hotel's restaurant, as it was a bit too...
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Hampton Inn Winchester-North
#3 Hotel in Winchester
Hampton Inn Winchester-North
The location of this hotel was excellent for vacationing in the Winchester area. Close to highways and Old Town Winchester. A good variety for the complimentary breakfast, but not...
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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.