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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 9,323 reviews and posted 3,032 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
This hotel has pretty basic rooms, however the staff make the experience more than worth while. Their professionalism and attentiveness to detail is unheard of. Everyone was...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
Stayed here for 2 nights and enjoyed breakfast one morning. Very pleasant and staff were friendly. The downtown location was good for us as we just parked our car and walked to...
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Hampton Inn Winchester-University/Mall Area
#3 Hotel in Winchester
Hampton Inn Winchester-University/Mall Area
Stopped here for a night during I-81 road trip. Flawless stay. Friendly check-in staff, recently-renovated room was top-notch...everything "works" (TV, furnishings, firm bed...
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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.