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 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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Our pick of the best Castlewood Hotel Deals

GuestHouse Lexington

GuestHouse Lexington

2261 Elkhorn Road Lexington KY
Fully refundable
NZ$139
12 Oct - 13 Oct
includes taxes & fees
GuestHouse Lexington
21c Museum Hotel Lexington

21c Museum Hotel Lexington

167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
NZ$292
1 Nov - 2 Nov
includes taxes & fees
21c Museum Hotel Lexington
The Manchester

The Manchester

941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
NZ$420
1 Nov - 2 Nov
includes taxes & fees
9.6/10 Exceptional! (1,423 reviews)
"Beautiful hotel, great staff"

Reviewed on 7 Oct 2026

The Manchester
See all 876 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.

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

NZ$103
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

NZ$173
per adult
100% of travellers recommend
Lexington: Downtown Walking Food & History Tour
Distillery District Food & History Tour in Lexington

Distillery District Food & History Tour in Lexington

NZ$218
per adult
Distillery District Food & History Tour in Lexington
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.