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Winchester Holiday Packages

Winchester, VA Courthouse
Old Town WInchester
A really cool old house across from the library.
Winchester Holiday Packages
Want to book a holiday to Winchester? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Winchester holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Winchester on TripAdvisor by comparing Winchester hotel and flight prices. Travellers like you have written 11,819 reviews and posted 1,060 candid photos for Winchester hotels. Book your Winchester holiday today!
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Country Inn & Suites By Carlson, Winchester
#1 Hotel in Winchester
Country Inn & Suites By Carlson, Winchester
Wonderfully comfortable room, large bed and top drawer all the way. The staff were very helpful and location excellent. The hotel could be a center of your mountain...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
“Elegant Hotel” 16/10/2017
Absolutely beautiful hotel.in downtown Winchester. Gorgeous room and bathroom. The pool is fantastic. Unfortunately, the bed was uncomfortable and bouncy. Too soft. Terrible night...
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Wingate by Wyndham Winchester
#3 Hotel in Winchester
Wingate by Wyndham Winchester
This was our home away for a wedding we attended. We brought our instruments and sound equipment. Even practiced in the room. It was a nice stay.
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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 travellers 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.