Castlewood

Lexington

Aerial view of the bridge over the Kentucky River on the road between Harrodsburg and Lexington, showcasing a forest-covered valley surrounded by agricultural fields in Central Kentucky.

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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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
Makers Mark, Four Roses or Woodford Reserve or Bulleit or Others

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

S$279
per adult
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others
Woodford Reserve, Castle & Key, and Stitzel Weller Bourbon Tour

Woodford Reserve, Castle & Key, and Stitzel Weller Bourbon Tour

S$363
per adult
Woodford Reserve, Castle & Key, and Stitzel Weller Bourbon Tour
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
See all activities in Lexington

Where to stay in Castlewood

Find the best Castlewood areas for the activities you enjoy most.
A city skyline with illuminated buildings and a church spire.
Photo by Jeff Rogers /Lexington Convention and Visitors Bureau
Open Photo by Jeff Rogers /Lexington Convention and Visitors Bureau

Downtown Lexington

While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.

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.

A white wooden fence leading to a large building with two towers.
Photo by Lexington Convention and Visitors Bureau/Gene Burch
Open Photo by Lexington Convention and Visitors Bureau/Gene Burch

Northside District

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

A grand building with large wooden doors and a sign reading "First Methodist Episcopal Church South."
Photo by Hyelsinta
Open Photo by Hyelsinta

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.

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.

Castlewood