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Winchester Vacation Packages

Rock to jump off of
Outside of restaurant
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Winchester Vacation Packages
Want to book a vacation to Winchester? Whether you're 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 1,069 reviews and posted 639 candid photos for Winchester hotels. Book your Winchester vacation today!
Or build your own Winchester vacation package
Hampton Inn Winchester
#1 Hotel in Winchester
Hampton Inn Winchester
We may plan our next trip to be able to stay here. It is conveniently located near the highway. The staff is outstanding. The comfort of the room and bedding the best! We usually...
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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 travelers in the past 72 hours*
Apr
$313 round trip
May
$80 round trip
Jun
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 travelers 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.