Castlewood Vacations

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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 Explorium.

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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 parade with people in colorful costumes on a wet street.

Northside District

If you're spending some time in Northside District, Lexington Opera House and West Sixth Brewing 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 might 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

If you're looking for some top things to see and do in Beaumont Residential and surrounding area, you can visit Kentucky Aviation Museum and Keeneland Racing Course.

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Castlewood Hotel Deals

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
NT$3,318
NT$3,851 total
Oct 11 - Oct 12
includes taxes & fees
Holiday Inn Express Lexington - Horse Park Area by IHG
Hyatt Regency Lexington

Hyatt Regency Lexington

401 W High St Lexington KY
NT$4,818
NT$5,592 total
Oct 25 - Oct 26
includes taxes & fees
Hyatt Regency Lexington
21c Museum Hotel Lexington

21c Museum Hotel Lexington

167 West Main Street Lexington KY
NT$5,105
NT$6,085 total
Oct 12 - Oct 13
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Excellent service!"

Reviewed on 2026/9/29

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 horseback 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.