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
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

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

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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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Our pick of the best 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
AU$162
3 Nov - 4 Nov
includes taxes & fees
9.4/10 Exceptional! (2,236 reviews)
"The room was awesome and very comfortable. Love the soap dispensers in the bathroom. Very handy. Front desk was very helpful"

Reviewed on 5 Oct 2026

Holiday Inn Express Lexington - Horse Park Area by IHG
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
AU$214
11 Oct - 12 Oct
includes taxes & fees
Marriott Lexington Griffin Gate Golf Resort & Spa
GuestHouse Lexington

GuestHouse Lexington

2261 Elkhorn Road Lexington KY
Fully refundable
AU$112
28 Oct - 29 Oct
includes taxes & fees
GuestHouse Lexington
See all 875 properties in Castlewood
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.
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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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Activities

Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

AU$83
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

AU$139
per adult
100% of travellers recommend
Lexington: Downtown Walking Food & History Tour
Bites of the Bluegrass Cocktails & Bites Tour

Bites of the Bluegrass Cocktails & Bites Tour

AU$176
per adult
100% of travellers recommend
Bites of the Bluegrass Cocktails & Bites Tour
See all activities in Lexington
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.