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

Winchester Vacation Packages

Stonewall Jackson Headquarters Museum
Old Town WInchester
A really cool old house across from the library.
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 10,255 reviews and posted 3,533 candid photos for Winchester hotels. Book your Winchester vacation today!
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Country Inn & Suites By Carlson, Winchester
#1 Hotel in Winchester
Country Inn & Suites By Carlson, Winchester
Stayed two nights while visiting friends. The hotel was clean and comfortable, and the staff went made every effort to be friendly and accomodating. The hot breakfast was good...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
This hotel was beautiful! We had a Jr. Suite with a fireplace and a jetted tub. The room was beautiful, and the bed was very comfortable. The location is excellent. We were within...
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Hampton Inn Winchester-University/Mall Area
#3 Hotel in Winchester
Hampton Inn Winchester-University/Mall Area
We stayed at this hotel as the halfway-point stopover for a trip from NY to NC - and it was perfect! Totally modern rooms and bathrooms, great breakfast (as always for Hampton...
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Cheap Flights to Winchester
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†  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.