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New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

Winchester Holiday Packages

Rock to jump off of
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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 1,030 reviews and posted 585 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
Everything is always clean and fresh. The evening appetizers and breakfast are welcome for weary travelers! The staff is helpful and friendly and willing to accomodate special...
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BEST WESTERN Winchester Hotel
#2 Hotel in Winchester
BEST WESTERN Winchester Hotel
Stayed here for night. Very nice motel, clean and spacious room. Location was near my meeting location. Low traffic and quiet. Breakfast buffet was very nice and fresh. Would...
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Red Roof Inn Lexington - Winchester
#3 Hotel in Winchester
Red Roof Inn Lexington - Winchester
Stayed here while doing an event in Mt Sterling. Check in was easy and painless. All of the rooms are non smoking, so that was a plus for me. Room was clean. Furniture and...
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Cheap Flights to Winchester
All Washington to Lexington (WAS-LEX) fares found by travellers in the past 72 hours*
Dec
US$271 round trip
Jan
US$271 round trip
Feb
find price round trip
†  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.