Winchester Holidays
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Your Winchester Holiday
Take away the hard part of organising your next epic adventure with a Winchester holiday package. Whether you're visiting for its landmarks, food or other highlights, this city offers endless possibilities for fun. Every trip to Winchester needs a well-thought-out itinerary. Fill yours with attractions like Bluegrass Heritage Museum, Lykins Park and Southwind Golf Course. Your ultimate Winchester holiday is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style.
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, Community Park and Lykins Park |
Top hotels in Winchester
Hampton Inn Winchester
The Manchester
Friendly and attentive staff. Great location, bar and onsite restaurant.
Reviewed on 9 Feb 2026
DoubleTree Suites by Hilton Hotel Lexington
All of the above
Reviewed on 9 Feb 2026
Popular places to visit
University of Kentucky
Take a campus tour or just explore the area of University of Kentucky during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Kentucky Horse Park
Enjoy a trip to Kentucky Horse Park and popular activities such as horse riding in Lexington. 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.
What to do in Winchester
Experience Rebecca Ruth Chocolate Tour & Museum!
Groups: Makers Mark OR Buffalo Trace OR Woodford or Others
Lexington: Downtown Walking Food & History Tour
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- Bowen Holidays
- Buckley Wildlife Sanctuary & Audobon Center
- Buffalo Trace Distillery
- Visit Clay City
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- Jacobson Park
- Kentucky Horse Park
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- Kentucky State Capitol
- Kentucky Holidays
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- Lexington Holidays
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
