Winchester Vacations
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Find the Best Winchester Vacation Packages
Winchester Hotel Deals
Best Western Winchester Hotel
1307 W Lexington Ave, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is ₩130,896 per night from Oct 5 to Oct 6
₩130,896
₩144,300 total
Oct 5 - Oct 6
includes taxes & fees
8.4/10 Very Good! (974 reviews)
"Older establishment Clean, very quiet, lovely fresh breakfast. 100% will return"
Reviewed on Sep 20, 2025
Spark by Hilton Lexington Hamburg
2381 Buena Vista Rd, Lexington, KY
The price is ₩99,968 per night from Oct 28 to Oct 29
₩99,968
₩116,032 total
Oct 28 - Oct 29
includes taxes & fees
8.6/10 Excellent! (160 reviews)
"Clean"
Reviewed on Sep 25, 2025
GuestHouse Lexington
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is ₩91,483 per night from Oct 20 to Oct 21
₩91,483
₩106,185 total
Oct 20 - Oct 21
includes taxes & fees
8.2/10 Very Good! (1,381 reviews)
"The gentleman at the front dest was very helpfu I m"
Reviewed on Sep 25, 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
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
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.
