Castlewood Holidays
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Where to stay in Castlewood
Downtown Lexington
While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.
Top hotels in Castlewood
The Manchester
The beds were really uncomfortable, it feels like they never rotate the mattress and it has a sunken place that makes the bed lumpy and did not get a good nights sleep. It was also very loud and the sound from the hall etc. carried through the entire room making it hard to sleep. Despite being told ...
Reviewed on 28 Feb, 2026
DoubleTree Suites by Hilton Hotel Lexington
Everything was nice.
Reviewed on 23 Feb, 2026
Hilton Lexington/Downtown
Of the 4 Hilton's I stay in regularly in KY and TN, this one has room for improvement. Building is very old and was the most luxurious of the downtown hotels. Unfortunately all that was lost during a bad renovation. Property is not a luxury hotel at all. Problems everywhere. Horrible wall paper pealing ...
Reviewed on 28 Feb, 2026
Popular places to visit
Keeneland Racing Course
Enjoy a trip to Keeneland Racing Course and popular activities such as horse riding in Lexington. You can attend a sporting event while in the area.
Rupp Arena
Catch an event at Rupp Arena and enjoy other activities in Lexington such as horse riding.Attend a sporting event or simply enjoy the lively bars while you're in the area.
Things to do
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Experience Rebecca Ruth Chocolate Tour & Museum!
Unique Horse Farm Tours with Insider Access to Private Farms
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.