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Winchester Hotel + Air Packages

Stonewall Jackson Headquarters Museum
Old Town WInchester
A really cool old house across from the library.
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Find the perfect vacation package for Winchester on TripAdvisor by comparing Winchester hotel and flight prices. Travelers like you have written 5,359 reviews and posted 1,397 candid photos for Winchester hotels. Book your Winchester vacation today!
Country Inn & Suites Winchester
#1 Hotel in Winchester
Country Inn & Suites Winchester
“No complaints” 09/01/2014
This hotel was great for what we needed. A quick 2 night stay. The hotel was pretty busy while we were there and the parking lot was full both nights of our stay. The room was...
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The George Washington Hotel
#2 Hotel in Winchester
The George Washington Hotel
“A Great Hotel” 09/01/2014
We stayed at the George Washington for two nights recently and found it a great choice. It is centrally located within walking distance from many restaurants and shops. It is...
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Holiday Inn Winchester Southeast-Historic Gateway
#3 Hotel in Winchester
Holiday Inn Winchester Southeast-Historic Gateway
Pros Nice and clean. Fast Check in. Close to interstate. Friendly staff. Free in room wifi Cons Cleaning people start cleaning rooms early and were a little loud. No free...
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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.