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
Holiday Inn Express Lexington Horse Park Area by IHG
It was a great experience. Would stay there again
Reviewed on 10 Mar 2026
The Manchester
We booked a deluxe room and there was NOTHING deluxe about it. The commode was not attached to the wall and banged against the wall every time you sat down or stood up. There were black smudge fingerprints on the ceiling. Per the description, we were going to get a couples massage but they no longer ...
Reviewed on 10 Mar 2026
Elwood Hotel & Suites
Friendly staff that got us checked in early. Our room was cleaned and organized while we were out exploring the city. The restaurant had amazing food and the ordering process was quick and easy. I would highly recommend coming here instead of the big name hotels.
Reviewed on 10 Mar 2026
Discover the most popular places to visit in Winchester
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.
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.
What to do in Winchester
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington: Downtown Walking Food & History Tour
