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$163 per night from 6 July to 7 July
NZ$163
6 July - 7 July
includes taxes & fees
7.2/10 Good! (806 reviews)
"Shower dirty hairs all over the walls"
Reviewed on 1 June 2026
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
100 Canebrake Drive Lexington KY
Fully refundableReserve now, pay when you stay
The price is NZ$181 per night from 14 June to 15 June
NZ$181
14 June - 15 June
includes taxes & fees
8.8/10 Excellent! (1,166 reviews)
"The property was clean and the people were friendly, but one of the reasons we chose this place was because they offered cribs and we're traveling with twin babies. It turns out, they actually have just one pack-and-play (they had two, but one is broken). We had to figure out how to make our own ..."
Reviewed on 6 June 2026
Hilton Lexington/Downtown
369 West Vine Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is NZ$245 per night from 4 July to 5 July
NZ$245
4 July - 5 July
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"Nice"
Reviewed on 3 June 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
Kentucky Horse Park is a popular place to visit in Lexington and nearby activities include horse riding. 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$99
per adult
90% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum!
NZ$17
per adult
80% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum
NZ$17
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.
