Castlewood Travel Guide
Lexington
Visit Castlewood
Popular places to visit
Kentucky Horse Park
Enjoy a trip to Kentucky Horse Park and popular activities such as horse riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
University of Kentucky
Take a campus tour or just explore the area of University of Kentucky during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Keeneland Racing Course
Enjoy a trip to Keeneland Racing Course and popular activities such as horse riding in Lexington. You can attend a sporting event while in the area.
Buffalo Trace Distillery
You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while in the area.
Lexington Convention Center
Learn about the events happening in Lexington Convention Center during your trip to Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Rupp Arena
Catch an event at Rupp Arena and enjoy other activities in Lexington such as horse riding.Attend a sporting event or simply enjoy the lively bars while you're in the area.
Things to do
Unique Horse Farm Tours with Insider Access to Private Farms
Experience Rebecca Ruth Chocolate Tour & Museum!
Seasonal Cooking and Entertaining with The Mischief Maker
Lexington: Downtown Walking Food & History Tour
Buffalo Trace, Bulleit, Pappy & Co. and Rabbit Hole Bourbon Tour
Top hotels in Castlewood
The Manchester
"The room was clean and smelled really good the hotel was very nice and the staff was very friendly and helpful we didn’t eat there but we had drinks they where good"
Reviewed on 18 May 2026
Hotel LEX, Trademark Collection by Wyndham
"The room was clean, but the lighting in the room was terrible. The rooms appeared newly remodeled but lacked modern lighting. The pool area was very nice, clean and big. Overall it was okay..would I stay there again? No"
Reviewed on 14 May 2026
Holiday Inn Express Lexington Horse Park Area by IHG
"Clean, and friendly staffs"
Reviewed on 18 May 2026
Hilton Lexington/Downtown
"Beautiful hotel in great location, walk to Rupp Arena! On event days parking garage can get very full, consider valet for a little extra and avoid the headache."
Reviewed on 18 May 2026
DoubleTree Suites by Hilton Hotel Lexington
Days Inn Lexington SE/Hamburg
"Was very outdated and room had roaches"
Reviewed on 17 May 2026
Other neighbourhoods around Castlewood
Bryan Station
While Bryan Station may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Legends Field and Loudoun House.
North Upper Street
Though North Upper Street may not have many top sights, you can venture to the surrounding area to see attractions like Lexington Opera House and Rupp Arena.
Martin Luther King
If you're spending some time in Martin Luther King, Lyric Theatre and Cultural Arts Center and The Kentucky Theater are top sights worth seeing.
Northside District
While visiting Northside District, you might make a stop by sights like Lexington Opera House and West Sixth Brewing.
Kenwick
While there might not be top attractions in Kenwick, you can explore the larger area and discover places like Ashland Henry Clay Estate and Lexington Opera House.
Downtown Lexington
While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.
