Castlewood Travel Guide
Lexington
Visit Castlewood
Popular places to visit
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.
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.
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.
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.
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.
Fayette Mall
You can do some window-shopping at Fayette Mall during your trip to Lexington. Discover the area's acclaimed theatre scene or seek out its horse riding.
Things to do
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington: Downtown Walking Food & History Tour
Experience Rebecca Ruth Chocolate Tour & Museum!
Bites of the Bluegrass Cocktails & Bites Tour
Distillery District Food & History Tour in Lexington
Groups: Makers Mark OR Buffalo Trace OR Woodford or Others
Top hotels in Castlewood
The Manchester
Beautiful room. Nice stay.
Reviewed on 16 Jan 2026
Spark by Hilton Lexington Hamburg
Very clean room and great amenities.
Reviewed on 17 Jan 2026
DoubleTree Suites by Hilton Hotel Lexington
Clean room love this place
Reviewed on 17 Jan 2026
Hyatt Regency Lexington
Location to rupp is awesome
Reviewed on 22 Jan 2026
Elwood Hotel & Suites
Loved this stay! This hotel is adorable and great staff!
Reviewed on 21 Jan 2026
Embassy Suites by Hilton Lexington/UK Coldstream
Location is great Rooms are nice Breakfast is fabulous and staff is very friendly The only problem we’ve experienced in our 3 stays was parking while a conference was in the building. Every spot was double parked and when we asked we were told to find someplace in the grass and that we would have ...
Reviewed on 18 Jan 2026
Other neighbourhoods around Castlewood
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 Downtown Arts Center are top sights worth seeing.
Bell Court
When in Bell Court, you can plan a visit to Lexington Memorial Coliseum and Lyric Theatre and Cultural Arts Center, some noteworthy sights in the nearby area.
Northside District
While visiting Northside District, you might make a stop by sights like Lexington Opera House and Bluegrass Distillers Downtown Lexington.
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.
Fairway
While Fairway may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Ashland Henry Clay Estate and Lexington Memorial Coliseum.
