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$139 per night from 14 Jan to 15 Jan
NZ$139
14 Jan - 15 Jan
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
Hampton Inn Winchester
1025 Early Dr Winchester KY
The price is NZ$237 per night from 25 Jan to 26 Jan
NZ$237
25 Jan - 26 Jan
includes taxes & fees
9.2/10 Wonderful! (455 reviews)
Overall the hotel was good - very friendly staff, safe area, clean and presentable. I was quite surprised and astonished by the $75 pet fee - it is outrageous for adding a dog to add $75 to a $150 room. This also was not clearly presented during the booking process.
Reviewed on 4 Jan 2026
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
The price is NZ$152 per night from 27 Jan to 28 Jan
NZ$152
27 Jan - 28 Jan
includes taxes & fees
7/10 Good! (772 reviews)
Everything was perfect.
Reviewed on 27 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.
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
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
NZ$77
per adult
98% of travellers recommend
From Lexington: Kentucky Horse Farms Tour
NZ$102
per adult
100% of travellers recommend
Buffalo Trace,Four Roses,Woodford,Bulleit Frontier/Stitzel, Castle&Key or Jeptha
NZ$413
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.
