Winchester Holidays
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Your Winchester Holiday
Our Winchester holiday packages give you the power to create your own adventure. Tailor your journey to your interests and style and make the most of your time in this wonderful city. You'll want to go sightseeing during your trip to Winchester. Drop by big-name attractions such as Lykins Park, Southwind Golf Course and Bluegrass Heritage Museum. Browse Expedia's wide range of travel options and book your ideal holiday to Winchester now.
Winchester Holiday
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Blue Grass Airport (LEX) |
Population | 18,400 |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Bluegrass Heritage Museum, Lykins Park and Southwind Golf Course |
Our pick of the best Winchester Hotel Deals
Best Western Winchester Hotel
This is our 2nd time staying here. Convenient stop on our trip. Rooms are clean and well maintained. The night check in guy Jared was very friendly & helpful.
Reviewed on 25 Nov 2025
Hilton Lexington/Downtown
Room was okay, however room service was non existent when we checked in. We needed to eat before our show and you say you provide that service no body answering the phone no message called front desk said they are busy so tried again a bit later ended up having to door dash which I did not want to ...
Reviewed on 7 Dec 2025
GuestHouse Lexington
A quiet clean place as always
Reviewed on 8 Dec 2025
Discover the most popular places to visit in Winchester
The Kentucky Castle
Enjoy a trip to The Kentucky Castle and popular activities such as horse riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Buffalo Trace Distillery
You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while in the area.
Rupp Arena
Catch an event at Rupp Arena and enjoy other activities in Lexington such as horse riding.Attend a sporting event or simply enjoy the lively bars while you're in the area.
What to do in Winchester
Unique Horse Farm Tours with Insider Access to Private Farms
Bites of the Bluegrass Cocktails & Bites Tour
