Castlewood Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Our guide on where to stay in Castlewood
Find the best Castlewood areas and neighborhoods for the activities you enjoy most. Learn more about Castlewood
Downtown Lexington
1 out of top 10 points of interest in this area
While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.
Our pick of the best Castlewood Hotel Deals
Quality Inn Lexington -Horse Park
1938 Stanton Way, Bldg A, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is NZ$123 per night from 31 Aug to 1 Sept
NZ$123
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (1,650 reviews)
Good hotel
"Nice budget hotel. No rowdy, loud guests. I would return"
Reviewed on 12 Aug. 2025
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is NZ$223 per night from 24 Aug to 25 Aug
NZ$223
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Doubletree
"Towels were hard could have Ben soft fan in the room did not work as well but other than that it was clean and spacious"
Reviewed on 12 Aug. 2025
The Manchester
941 Manchester St, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is NZ$393 per night from 31 Aug to 1 Sept
NZ$393
31 Aug - 1 Sept
includes taxes & fees
9.4/10 Exceptional! (951 reviews)
"What a gem of a hotel! My husband and I wanted a nice hotel to stay during our cross-country road trip and this was perfect. We arrived at 8:30pm, checked in quickly and were at the rooftop bar by 9pm. Dinner and drinks were delicious and the atmosphere was great. The room itself was cozy and swanky ..."
Reviewed on 12 Aug. 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 Castlewood
Kentucky Horse Park
Explore Kentucky Horse Park, a favourite green space in Lexington, and also enjoy the area's 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.
The Red Mile Racetrack
Enjoy a trip to The 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.
Activities
Experience Rebecca Ruth Chocolate Tour & Museum!
NZ$17
per adult
Unique Horse Farm Tours with Insider Access to Private Farms
NZ$81
per adult
86% of travellers recommend
Lexington: Downtown Walking Food & History Tour
NZ$165
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.