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
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.
Reviewed on 14 Dec 2025
Hampton Inn Winchester
Overall the hotel was good - very friendly staff, safe area, clean and presentable. I was quite surprised and astonished by the $75 pet fee - it is outrageous for adding a dog to add $75 to a $150 room. This also was not clearly presented during the booking process.
Reviewed on 4 Jan 2026
The Manchester
Great place to stay, eat and drink.
Reviewed on 20 Jan 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
Bites of the Bluegrass Cocktails & Bites Tour
