Winchester Holidays
Photo by Nawa Aseen
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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 €84 per night from 1 Jan to 2 Jan
€84
1 Jan - 2 Jan 2026
includes taxes & fees
8.4/10 Very Good! (999 reviews)
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.
Reviewed on 14 Dec 2025
Holiday Inn Express Lexington East - Winchester by IHG
100 Winchester Plaza Winchester KY
Fully refundable
The price is €82 per night from 4 Jan to 5 Jan
€82
4 Jan - 5 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (526 reviews)
Very friendly staff. Room was clean and spacious.
Reviewed on 22 Dec 2025
Hampton Inn Winchester
1025 Early Dr Winchester KY
The price is €107 per night from 30 Dec to 31 Dec
€107
30 Dec - 31 Dec
includes taxes & fees
9.2/10 Wonderful! (452 reviews)
Enjoyed our stay.
Reviewed on 6 Dec 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
Enjoy a trip to Kentucky Horse Park and popular activities such as horse riding in Lexington. 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
80% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
€50
per adult
90% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum
€9
per adult
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