Castlewood Holidays
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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.
Top hotels in Castlewood
Hyatt Regency Lexington
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
€135
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (1,017 reviews)
"Stayed for Lexington Comic Con so we could travel back in forth inside which was nice. Also within steps of Lex Live. Breakfast was delicious inside property. The pool area was clean with plenty of towels and water was great temperature. Hyatt made our stay very comfortable."
Reviewed on 6 Sept 2026
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
€128
20 Sept - 21 Sept
includes taxes & fees
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
€225
28 Sept - 29 Sept
includes taxes & fees
9.6/10 Exceptional! (1,420 reviews)
"Delaney at checkin was excellent- great recommendation for our trip shared. Valet team were A+ accommodating our frequent in and outs efficiently and with friendly conversation. Thank you! - Danielle"
Reviewed on 7 Sept 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.
Things to do
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others
€190
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
€9
per adult
80% of travellers recommend
Lexington: Downtown Walking Food & History Tour
€86
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.