Winchester Vacations
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Find the Best Winchester Vacation Packages
Winchester Hotel Deals
Value Stay
5100 Revilo Rd, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is ￥9,118 per night from Dec 8 to Dec 9
￥9,118
￥10,051 total
Dec 8 - Dec 9
includes taxes & fees
7.6/10 Good! (123 reviews)
Nice place. Clean rooms
Reviewed on Oct 28, 2025
Best Western Winchester Hotel
1307 W Lexington Ave, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is ￥12,478 per night from Nov 20 to Nov 21
￥12,478
￥13,756 total
Nov 20 - Nov 21
includes taxes & fees
8.4/10 Very Good! (996 reviews)
Super nice! Great staff and great breakfast! Super clean!
Reviewed on Nov 13, 2025
Hilton Lexington/Downtown
369 West Vine Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is ￥18,883 per night from Nov 30 to Dec 1
￥18,883
￥21,918 total
Nov 30 - Dec 1
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
Good
Reviewed on Nov 9, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Winchester
Kentucky Horse Park
4.5/5(328 reviews)
Enjoy a trip to Kentucky Horse Park and popular activities like horseback riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
University of Kentucky
4.5/5(384 reviews)
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
4.5/5(321 reviews)
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
Experience Rebecca Ruth Chocolate Tour & Museum!
￥1,527
per adult
Groups: Makers Mark OR Buffalo Trace OR Woodford or Others
￥27,477
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
