Castlewood Travel Guide
Tourist Guide
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.
Activities
Bourbon Tour (03) : Buffalo Trace, Woodford, Four Roses, Wild Turkey, Other
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Unique Horse Farm Tours with Insider Access to Private Farms
Experience Rebecca Ruth Chocolate Tour & Museum!
Experience Rebecca Ruth Chocolate Tour & Museum
Sound Bath Meditation in Lexington
Our pick of the best Castlewood Hotel Deals
The Manchester
"Had a great overnight stay. Shuttle was great to Distillary area and dining room rooftop was nice. We even played Trivia that night ( ugh we lost). Great nights rest before heading to Nashville. Would stay there again for certain."
Reviewed on 18 May 2026
Hotel LEX, Trademark Collection by Wyndham
"Ended up getting a refund as my son ended up having an allergic reaction. Staff were not accommodating in person but contacted the owner after we left who understood our situation."
Reviewed on 20 May 2026
Holiday Inn Express Lexington Horse Park Area by IHG
"Love the plank flooring for traveling with a dog!"
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
"Very pleasant stay. The staff was exceptional"
Reviewed on 19 May 2026
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 Memorial Coliseum.
Downtown Lexington
While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.
