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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 7,234 reviews and posted 2,256 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
The room was clean. Our mini schnauzer settled in like it was home. Unfortunately, I got a migraine and my husband had an asthma attack. We think it was from the cleaning...
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The George Washington A Wyndham Grand Hotel
#2 Hotel in Winchester
The George Washington A Wyndham Grand Hotel
It's a lovely hotel. Unfortunately I left a favorite pair of sandals in the room. I know exactly where I left them and reported it. But housekeeping claims not to have found them.
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Hampton Inn Winchester-North
#3 Hotel in Winchester
Hampton Inn Winchester-North
Hampton Inn is a budget, limited service product of Hilton. As the saying goes, what could possibly go wrong? However, in this case, the experience was flawless, from breakfast...
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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.