Castlewood Trip

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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
A parade with people in colorful costumes on a wet street.

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.

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A parade with people in colorful costumes on a wet street.

Northside District

While visiting Northside District, you might make a stop by sights like Lexington Opera House and West Sixth Brewing.

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A river with a bridge, a town with historic buildings, and a hilly landscape in the background.

Liberty Area

If you're spending some time in Liberty Area, Hamburg Place and Hamburg Pavilion are top sights worth seeing.

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A grand building with large wooden doors and a sign reading "First Methodist Episcopal Church South."

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.

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A paved pathway flanked by trees and a wooden fence.

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.

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Top hotels in Castlewood

Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG

1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
₹9,875
₹11,462 total
29 Sept - 30 Sept
includes taxes & fees
Holiday Inn Express Lexington - Horse Park Area by IHG
Hyatt Regency Lexington

Hyatt Regency Lexington

401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
₹12,951
₹15,032 total
27 Sept - 28 Sept
includes taxes & fees
Hyatt Regency Lexington
21c Museum Hotel Lexington

21c Museum Hotel Lexington

167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
₹13,129
₹15,718 total
29 Sept - 30 Sept
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Loved sleeping in an art museum."

Reviewed on 19 Sept 2026

21c Museum Hotel Lexington
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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.
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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.
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