Winchester Holidays
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Top hotels in Winchester
Best Western Winchester Hotel
1307 W Lexington Ave, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is €72 per night from 29 Sept to 30 Sept
€72
29 Sept - 30 Sept
includes taxes & fees
8.4/10 Very Good! (974 reviews)
"Older establishment Clean, very quiet, lovely fresh breakfast. 100% will return"
Reviewed on 20 Sept 2025
GLō Best Western Lexington
1935 Stanton Way, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is €96 per night from 5 Oct to 6 Oct
€96
5 Oct - 6 Oct
includes taxes & fees
9.2/10 Wonderful! (2,260 reviews)
"Love the place"
Reviewed on 19 Sept 2025
Hilton Lexington/Downtown
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is €163 per night from 5 Oct to 6 Oct
€163
5 Oct - 6 Oct
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
Great stay
"Great location. Close to all the good attractions"
Reviewed on 21 Sept 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.
Popular places to visit
Kentucky Horse Park
4.5/5(5 reviews)
Kentucky Horse Park is a popular place to visit in Lexington and nearby activities include horse riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.
The Kentucky Castle
Enjoy a trip to The Kentucky Castle and popular activities such as horse riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.
What to do in Winchester
Experience Rebecca Ruth Chocolate Tour & Museum!
€9
per adult
Lexington: Downtown Walking Food & History Tour
€84
per adult
Unique Horse Farm Tours with Insider Access to Private Farms
€42
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
