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Winchester Holiday Packages

Rock to jump off of
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red river gorge bridge
Winchester Holiday Packages
Want to book a vacation to Winchester? Whether you are 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 1,097 reviews and posted 703 candid photos for Winchester hotels. Book your Winchester vacation today!
Or build your own Winchester holiday package
Hampton Inn Winchester
#1 Hotel in Winchester
Hampton Inn Winchester
This Hampton Inn had a friendly staff, clean rooms, wonderful breakfast and even provided light food in the evening. One night they had wings, another night you could make...
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BEST WESTERN Winchester Hotel
#2 Hotel in Winchester
BEST WESTERN Winchester Hotel
The room was very clean and had comfortable beds. The staff were very friendly and accommodating. The breakfast was delicious and had so many options. The fruit was very fresh...
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Red Roof Inn Lexington - Winchester
#3 Hotel in Winchester
Red Roof Inn Lexington - Winchester
The Red Roof Inn in Winchester did an awesome job of providing a great clean room with a quick access door to the outside for our pet friendly convenience! We are really grateful...
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Cheap Flights to Winchester
All Washington to Lexington (WAS-LEX) fares found by travellers in the past 72 hours*
May
US$74 return
Jun
find price return
Jul
US$99 return
†  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.