Winchester Holidays
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Winchester Holiday
Our pick of the best Winchester Hotel Deals
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
The price is NZ$153 per night from 30 Apr to 1 May
NZ$153
30 Apr - 1 May
includes taxes & fees
7.2/10 Good! (791 reviews)
The hotel provides value for the cost. Staff, facilities, and maintenance were above average for a budget hotel.
Reviewed on 22 Apr 2026
Spark by Hilton Lexington Hamburg
2381 Buena Vista Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is NZ$145 per night from 17 May to 18 May
NZ$145
17 May - 18 May
includes taxes & fees
8.8/10 Excellent! (444 reviews)
The only thing discouraging was the fact that the shower water was never hot. It was luke warm which was horrible.
Reviewed on 23 Apr 2026
Holiday Inn Express Lexington Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is NZ$194 per night from 3 May to 4 May
NZ$194
3 May - 4 May
includes taxes & fees
9.4/10 Exceptional! (2,186 reviews)
Hotel was updated and clean. Laid out different than most with the beds right at the door when you walk into the room rather than the bathroom first. The walls are thin so the hallway noise and doors shutting were loud as the bed shares the hallway wall. AC unit in room was super loud kicking on ...
Reviewed on 24 Apr 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.
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
Bourbon Tour (03) : Buffalo Trace, Woodford, Four Roses, Wild Turkey, Other
NZ$321
per adult
86% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
NZ$77
per adult
98% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
NZ$100
per adult
90% of travellers recommend
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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.
