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
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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Top hotels in Castlewood

GuestHouse Lexington

GuestHouse Lexington

2261 Elkhorn Road Lexington KY
Fully refundable
S$95
20 Oct - 21 Oct
includes taxes & fees
8.4/10 Very good! (1,682 reviews)
"Great last minute find. It was a Kentucky Football weekend, as well as Keenland Fall session. Good location, friendly staff, clean rooms and fair price. Bonus breakfast was included!"

Reviewed on 16 Oct, 2026

GuestHouse Lexington
21c Museum Hotel Lexington

21c Museum Hotel Lexington

167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
S$210
8 Nov - 9 Nov
includes taxes & fees
21c Museum Hotel Lexington
The Manchester

The Manchester

941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
S$276
15 Nov - 16 Nov
includes taxes & fees
The Manchester
See all 841 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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Things to do

Picture 1 for Activity Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

S$57
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others

Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others

S$281
per adult
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

S$126
per adult
100% of travellers recommend
Lexington: Downtown Walking Food & History Tour
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