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Your Winchester Vacation
Take away the hard part of organizing your next epic adventure with a Winchester vacation 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 vacation is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style.
The Latest Winchester vacation packages


21c Museum Hotel Lexington
Reviewed on Jul 13, 2025

Home2 Suites by Hilton Lexington University / Medical Center
Reviewed on Jun 30, 2025

MainStay Suites Georgetown Lexington North
Reviewed on Jun 26, 2025

Hyatt Regency Lexington
Reviewed on Jul 11, 2025
Discover the most popular places to visit in Winchester

Kentucky Horse Park
Experience the exciting worlds of horses and horseracing at this equine theme park with multiple museums in the middle of Kentucky’s horse country.

University of Kentucky
Explore the campus 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.

Fayette Mall
You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.
What to do in Winchester

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Experience Rebecca Ruth Chocolate Tour & Museum!

Lexington: Downtown Walking Food & History Tour
Winchester Hotel Deals

Reviewed on Jul 4, 2025

Reviewed on Jul 12, 2025

Reviewed on Jul 12, 2025
Find the Best Winchester Vacation Packages
Winchester Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Closest Airport | Blue Grass Airport (LEX) |
Population | 18,400 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
Top Sights | Bluegrass Heritage Museum, Southwind Golf Course and Lykins Park |
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- Hotels near Bluegrass Heritage Museum
- Hotels near Community Park
- Hotels near Clark Regional Medical Center
- Hotels near Lykins Park
- Hotels near Southwind Golf Course
- Hotels near Cassell Creek Golf Course
- Hotels near Kentucky River Museum
- Hotels near Fort Boonesborough State Park
- Hotels near Grimes Mill Winery
- Hotels near Kentucky River
- Lexington Hotels
- Hotels near W S Webb Museum of Anthropology
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- Bluegrass Heritage Museum
- Lykins Park
- Southwind Golf Course
- Cassell Creek Golf Course
- Fort Boonesborough State Park
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- Raven Run Nature Sanctuary
- Jacobson Park
- Mount Sterling Vacations
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- White Hall State Historic Site
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- The Thoroughbred Center
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- Hopewell Museum
- The Cane Ridge Meeting House
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