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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 1,210 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
“Great hotel” 23/07/2017
We stopped at this hotel while driving through Kentucky to get home. We typically look for a Hampton Inn to stop at on our road trips because they are usually very dependable on...
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Best Western Winchester Hotel
#2 Hotel in Winchester
Best Western Winchester Hotel
“Perfect!” 26/07/2017
This hotel is a perfect example of how a hotel should be operated. The owners were proud of their hotel and rightfully so. The breakfast bar had so many selections of toppings...
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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
All Washington to Lexington (WAS-LEX) fares found by travellers in the past 72 hours*
Aug
USD 257 return
Sep
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Oct
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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.