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Winchester Holiday Packages

Shallow crossing
Movie night for the family. There was dancing, music and a family friendly feature film.
Winchester Holiday Packages
Want to book a holiday to Winchester? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Winchester holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Winchester on TripAdvisor by comparing Winchester hotel and flight prices. Travellers like you have written 1,369 reviews and posted 817 candid photos for Winchester hotels. Book your Winchester holiday today!
Or build your own Winchester holiday package
Hampton Inn Winchester
#1 Hotel in Winchester
Hampton Inn Winchester
I usually stay in Hamptons when traveling for work. This one is by far better than any other. Nice staff, clean room, comfortable bed, and a good night sleep. Breakfast offered...
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Best Western Winchester Hotel
#2 Hotel in Winchester
Best Western Winchester Hotel
My friend and I were traveling through Kentucky in the freezing snow and needed a couple warm, clean, reasonably priced rooms for the night so I checked the Tripadvisor reviews of...
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Red Roof Inn Lexington - Winchester
#3 Hotel in Winchester
Red Roof Inn Lexington - Winchester
When I arrived, in the rain and wind, at the end of a long day's drive, Donald C., a maintenance worker at the end of his shift, helped me unload and get my luggage to my room...
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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 travellers 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.