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Winchester Vacation Packages

red river gorge bridge
The Ale 8 machine had been broken into.
beer
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 540 reviews and posted 306 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
I stayed two nights here last week. I arrived early. They let me check in without issue. The hotel is very clean. The staff was great. The pool was really nice. The location is...
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BEST WESTERN Country Squire
#2 Hotel in Winchester
BEST WESTERN Country Squire
Due to construction on the road leading to the hotel, it was hard to find. I would suggest that you call for directions. GPS did not recognize construction. Rooms have already...
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Quality Inn & Suites Winchester
#3 Hotel in Winchester
Quality Inn & Suites Winchester
I spent the night here after a long day. This hotel did the job well. The rooms were clean and the staff members were friendly. This hotel was cheap, but still clean and kept up...
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Cheap Flights to Winchester
All Washington to Lexington (WAS-LEX) fares found by travelers in the past 72 hours*
Jul
$293 round trip
Aug
$261 round trip
Sep
$359 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.