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Winchester Holiday Packages

Rock to jump off of
red river gorge bridge
A view of the Gorge
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 1,200 reviews and posted 783 candid photos for Winchester hotels. Book your Winchester holiday today!
Or build your own Winchester holiday package
Hampton Inn Winchester
#1 Hotel in Winchester
Hampton Inn Winchester
Nice and relaxing stay. The dinner served that evening was a nice surprise! The rooms were super nice and bathroom were huge. Loved the outdoor pool.Book the stay online. It was...
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Best Western Winchester Hotel
#2 Hotel in Winchester
Best Western Winchester Hotel
After being on the road for 2 weeks, it was good to find a Best Western that was a reasonable price. Nothing fancy, but very nice. Comfortable, good pool, very nice staff, and a...
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Red Roof Inn Lexington - Winchester
#3 Hotel in Winchester
Red Roof Inn Lexington - Winchester
This is an older motel, but was very comfortable, clean, an worth the effort. The desk clerk was helpful and friendly. Arrived at 11 pm and got a king room that was a little...
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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 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.