Castlewood Holidays
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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
2 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
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is NZ$382 per night from 25 Feb to 26 Feb
NZ$382
25 Feb - 26 Feb
includes taxes & fees
9.4/10 Exceptional! (1,161 reviews)
Friendly and attentive staff. Great location, bar and onsite restaurant.
Reviewed on 9 Feb 2026
Hyatt Regency Lexington
401 W High St Lexington KY
The price is NZ$277 per night from 22 Feb to 23 Feb
NZ$277
22 Feb - 23 Feb
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
Room was great! Staff was awesome. Being able to go into Rupp without going outside, the best.
Reviewed on 9 Feb 2026
Elwood Hotel & Suites
444 Parkway Drive Lexington KY
Fully refundableReserve now, pay when you stay
The price is NZ$172 per night from 22 Feb to 23 Feb
NZ$172
22 Feb - 23 Feb
includes taxes & fees
9.4/10 Exceptional! (1,027 reviews)
Wonderful Stay! Room was clean. Staff was very nice.
Reviewed on 11 Feb 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 Castlewood
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.
Activities
Lexington: Downtown Walking Food & History Tour
NZ$167
per adult
Distillery District Food & History Tour in Lexington
NZ$167
per adult
Unique Horse Farm Tours with Insider Access to Private Farms
NZ$98
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.