Winchester Holidays
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Top hotels in Winchester
Hampton Inn Winchester
1025 Early Dr Winchester KY
The price is €110 per night from 15 Feb to 16 Feb
€110
15 Feb - 16 Feb
includes taxes & fees
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is €172 per night from 8 Mar to 9 Mar
€172
8 Mar - 9 Mar
includes taxes & fees
9.6/10 Exceptional! (1,161 reviews)
Friendly and attentive staff. Great location, bar and onsite restaurant.
Reviewed on 9 Feb 2026
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is €108 per night from 19 Feb to 20 Feb
€108
19 Feb - 20 Feb
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
All of the above
Reviewed on 9 Feb 2026
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)
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!
€8
per adult
80% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
€49
per adult
90% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum
€8
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
