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.
Northside District
While visiting Northside District, you might make a stop by sights like Lexington Opera House and West Sixth Brewing.
Liberty Area
If you're spending some time in Liberty Area, Hamburg Place and Hamburg Pavilion are top sights worth seeing.
Picadome
While there might not be top attractions in Picadome, you can explore the larger area and discover places like Kroger Field and Red Mile Racetrack.
Historic South Hill
While Historic South Hill may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lexington Memorial Coliseum and Rupp Arena.
Our pick of the best Castlewood Hotel Deals
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
NZ$205
6 Sept - 7 Sept
includes taxes & fees
8.8/10 Excellent! (1,045 reviews)
"Very spacious, clean room. Perfect option for move-in at UK."
Reviewed on 24 Aug 2026
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
NZ$339
7 Sept - 8 Sept
includes taxes & fees
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
NZ$234
6 Sept - 7 Sept
includes taxes & fees
8.4/10 Very good! (824 reviews)
"The restaurant was understaffed and took forever to wait on us and even longer to bring our food and it wasn’t busy. The room had temporary fans in it and it appeared the sliding door to the balcony had been leaking. The next day I broke out in a rash from head to toe. This was probably a good place ..."
Reviewed on 25 Aug 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.
Stay near popular Castlewood attractions
Loudoun House
Find out about the history of Lexington when you take a trip to Loudoun House. Make time for the shops and horse riding in this family-friendly area.
Castlewood Park
Castlewood Park is just one of the places to see in Lexington, so why not enjoy the other things to explore during your travels? Attend a sporting event or visit the shops in this family-friendly area.
Activities
Lexington: Downtown Walking Food & History Tour
NZ$171
per adult
100% of travellers recommend
Distillery District Food & History Tour in Lexington
NZ$216
per adult
Unique Horse Farm Tours with Insider Access to Private Farms
NZ$102
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.