Winchester Holidays
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Winchester Holiday
Our pick of the best Winchester Hotel Deals
Best Western Winchester Hotel
1307 W Lexington Ave Winchester KY
Fully refundableReserve now, pay when you stay
The price is NZ$159 per night from 25 Nov to 26 Nov
NZ$159
25 Nov - 26 Nov
includes taxes & fees
8.4/10 Very Good! (996 reviews)
Super nice! Great staff and great breakfast! Super clean!
Reviewed on 13 Nov 2025
Hyatt Regency Lexington
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
The price is NZ$277 per night from 29 Nov to 30 Nov
NZ$277
29 Nov - 30 Nov
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
Very clean
Reviewed on 17 Nov 2025
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is NZ$327 per night from 21 Dec to 22 Dec
NZ$327
21 Dec - 22 Dec
includes taxes & fees
9.4/10 Exceptional! (1,045 reviews)
We had a wonderful stay. The hotel was beautiful. The room was well decorated, and the bedding was comfortable. We loved the lounge and the service was excellent. We will definitely return.
Reviewed on 14 Nov 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
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.
Red Mile Racetrack
Enjoy a trip to Red Mile Racetrack 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.
What to do in Winchester
Unique Horse Farm Tours with Insider Access to Private Farms
NZ$85
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
NZ$172
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
NZ$17
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
