Winchester Vacations
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- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
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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 ₩85,780 per night from Dec 1 to Dec 2
₩85,780
₩94,561 total
Dec 1 - Dec 2
includes taxes & fees
7.6/10 Good! (124 reviews)
Great
Reviewed on Nov 15, 2025
Best Western Winchester Hotel
1307 W Lexington Ave, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is ₩117,387 per night from Nov 23 to Nov 24
₩117,387
₩129,407 total
Nov 23 - Nov 24
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 ₩177,636 per night from Nov 30 to Dec 1
₩177,636
₩206,182 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
The Kentucky Castle
4.5/5(24 reviews)
Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Kroger Field
4.5/5(136 reviews)
Catch an event at Kroger Field, and enjoy other activities in Lexington such as horseback riding. Experience the area's acclaimed theater scene or attend a sporting event.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
