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
Baymont by Wyndham Winchester
"Great people clean rooms and the pool works"
Reviewed on 8 June 2026
Holiday Inn Express Lexington Horse Park Area by IHG
"Bathroom sink was dirty and clearly not cleaned before we got there. Long blonde hair all over the sink. Shower was okay, just seemed a little dirty and not cleaned overall. Front staff was incredibly nice."
Reviewed on 9 June 2026
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
"They switched the price to three hundred a night. Double charged my card. The front desk was very rude when I Questioned it and the manager still has not called me back. Will be contacting the attorney general office and the BBB."
Reviewed on 9 June 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.
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.
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
Experience Rebecca Ruth Chocolate Tour & Museum!
