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Winchester Holiday Packages

Rock to jump off of
Fitness center
red river gorge bridge
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 1,070 reviews and posted 692 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
Exemplary service, helpful staff, clean rooms and a good breakfast- I will definitely use this hotel again, and recommend it to any travelling to the area. It was worth leaving...
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BEST WESTERN Winchester Hotel
#2 Hotel in Winchester
BEST WESTERN Winchester Hotel
I've stayed here before and they've recently refreshed the property and expanded the lobby area. Pleasantly surprised! I would definitely stay here again when I'm through the...
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Red Roof Inn Lexington - Winchester
#3 Hotel in Winchester
Red Roof Inn Lexington - Winchester
Not a bad place only downside was in the other room they saw a roach. When we talked with management they did everything they could to help. They gave us a 2 rooms at 11:00 at...
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Cheap Flights to Winchester
All Washington to Lexington (WAS-LEX) fares found by travellers in the past 72 hours*
Apr
USD 313 return
May
USD 80 return
Jun
find price 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.