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.
Liberty Area
If you're spending some time in Liberty Area, Hamburg Place and Hamburg Pavilion are top sights worth seeing.
Northside District
While visiting Northside District, you might make a stop by sights like Lexington Opera House and West Sixth Brewing.
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.
Beaumont Residential
While Beaumont Residential isn't home to many top sights, Kentucky Aviation Museum and Keeneland Racing Course are some notable places to visit nearby.
Top hotels in Castlewood
Holiday Inn Express Lexington - Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
Rp1.838.241
Rp2.133.787 total
29 Sept - 30 Sept
includes taxes & fees
9.4/10 Exceptional! (2,245 reviews)
"Super nice front desk staff, room was squeaky clean, breakfast was amazing! 10/10"
Reviewed on 22 Sept 2026
Hyatt Regency Lexington
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
Rp2.409.345
Rp2.796.527 total
28 Sept - 29 Sept
includes taxes & fees
21c Museum Hotel Lexington
167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
Rp2.443.879
Rp2.925.846 total
29 Sept - 30 Sept
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"We really enjoyed our stay at 21cMuseum Hotel. The location couldn't be beat. We were able to walk to great bars and restaurants nearby. The valet parking was a very convenient feature. The room was spacious and had a comfortable bed. The staff were all very kind and readily available. The gallery ..."
Reviewed on 21 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
Unique Horse Farm Tours with Insider Access to Private Farms
Rp1.035.273
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
Rp1.737.153
per adult
100% of travellers recommend
Woodford Reserve, Castle & Key, and Stitzel Weller Bourbon Tour
Rp4.990.635
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.