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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 5,288 reviews and posted 1,377 candid photos for Winchester hotels. Book your Winchester vacation today!
Country Inn & Suites Winchester
#1 Hotel in Winchester
Country Inn & Suites Winchester
My husband and I recently spent a long weekend at this hotel and everything was excellent except for the size of the breakfast room. The food was very good but it was crowded and...
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The George Washington Hotel
#2 Hotel in Winchester
The George Washington Hotel
We have stayed at the Wyndham George Washington Hotel numerous times and have always had an enjoyable stay. The staff is friendly and helpful. The rooms are small but nicely...
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Holiday Inn Winchester Southeast-Historic Gateway
#3 Hotel in Winchester
Holiday Inn Winchester Southeast-Historic Gateway
“Nice Enough” 08/21/2014
We arrived late after a long day on the road. It wasn't easy to find; I think it depends on what direction you are arriving from. The room was fine: quiet with comfortable beds...
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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.