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Winchester Vacation Packages

Yup we drove through that...
Flooded campsite
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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 516 reviews and posted 282 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
Found the Hampton online while traveling across the country. Rate was reasonable and it was along the way. My son and I checked in at close to midnight and the desk staff was...
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BEST WESTERN Country Squire
#2 Hotel in Winchester
BEST WESTERN Country Squire
Much work being done to remodel the exterior. Wasn't sure if we wanted to stay because of the work being done but took a chance. Staff was great and room was better than...
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Quality Inn & Suites Winchester
#3 Hotel in Winchester
Quality Inn & Suites Winchester
pool was closed, so that was a negative. Staff was friendly and very acomodating when i pulled in with my truck and livestock trailer even though they were full up on truck...
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Cheap Flights to Winchester
All Washington to Lexington (WAS-LEX) fares found by travelers in the past 72 hours*
Jun
$284 round trip
Jul
$264 round trip
Aug
$287 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.