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 Rupp Arena.

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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 horse grazing on a grassy field with a leafless tree in the background under a purple sky.

Picadome

While there might not be top attractions in Picadome, you can explore the larger area and discover places like Kroger Field and Red Mile Racetrack.

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Top hotels in Castlewood

Hyatt Regency Lexington

Hyatt Regency Lexington

401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
S$176
7 Sept - 8 Sept
includes taxes & fees
Hyatt Regency Lexington
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
S$178
6 Sept - 7 Sept
includes taxes & fees
Marriott Lexington Griffin Gate Golf Resort & Spa
The Manchester

The Manchester

941 Manchester St Lexington KY
S$276
7 Sept - 8 Sept
includes taxes & fees
9.6/10 Exceptional! (1,414 reviews)
"Amazing hotel and staff - highly recommend."

Reviewed on 31 Aug, 2026

The Manchester
See all 868 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
Buffalo Trace, Bulleit Distilling and Rabbit Hole Bourbon Tour

Buffalo Trace, Bulleit, Pappy & Co. and Rabbit Hole Bourbon Tour

S$349
per adult
Buffalo Trace, Bulleit, Pappy & Co. and Rabbit Hole Bourbon Tour
Woodford Reserve, Kismet Thoroughbred Farm & Whiskey Thief

Woodford Reserve, Kismet Thoroughbred Farm & Whiskey Thief

S$350
per adult
100% of travellers recommend
Woodford Reserve, Kismet Thoroughbred Farm & Whiskey Thief
See all activities in Lexington

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