Castlewood
Lexington
Visit Castlewood
Popular places to visit
Kentucky Horse Park
Kentucky Horse Park is a favorite place to visit in Lexington and nearby activities include horseback riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.
University of Kentucky
Explore the campus 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.
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 like horseback riding in Lexington. You can attend a sporting event while in the area.
Lexington Convention Center
Learn about the events happening at Lexington Convention Center during your trip to Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
The Kentucky Castle
Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Things to do
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Bourbon Tour (03) : Buffalo Trace, Woodford, Four Roses, Wild Turkey, Other
From Lexington: Kentucky Horse Farms Tour
Buffalo Trace,Four Roses,Woodford,Bulleit Frontier/Stitzel, Castle&Key or Jeptha
Experience Rebecca Ruth Chocolate Tour & Museum!
Unique Horse Farm Tours with Insider Access to Private Farms
Top hotels in Castlewood
The Manchester
"Restaurant was loud and food was way too salty, especially for a Michelin starred restaurant. Wait staff were slow and inattentive, tha salad plate and bread plates were still on the table thru and after dessert. To be fair, they did comp both of our entrees. Not a great birthday celebration."
Reviewed on May 28, 2026
Hilton Lexington/Downtown
"We loved it, it was very clean, safe, and spacious. We were able to go to the Rupp arena via the skybridge which was nice because it was raining!"
Reviewed on May 29, 2026
Holiday Inn Express Lexington Horse Park Area by IHG
"The staff was helpful, the room was clean, and we enjoyed our staff. Everything was close to the hotel, which was nice to have the restaurant close as well as gas station."
Reviewed on May 29, 2026
Hotel LEX, Trademark Collection by Wyndham
"This was my first stay at this hotel, and I booked it based on the positive reviews and photos online. Unfortunately, my experience was very different. While check-in was smooth, the first room was dark, damp, and dirty. There were ants coming from the AC unit, stains on the walls and unit, and what ..."
Reviewed on May 27, 2026
Quality Inn Lexington -Horse Park
"Staff was pleasant and helpful. Clean rooms. Hallway could have been updated. Good location"
Reviewed on May 28, 2026
DoubleTree Suites by Hilton Hotel Lexington
"Asked for room not to be cleaned and they did it anyway and my mess were thrown away or stolen.I also was charged for 39 dollars of parking I did not use"
Reviewed on May 30, 2026
Other neighbourhoods around Castlewood
North Upper Street
North Upper Street might not have many top sights, but Lexington Opera House and Rupp Arena are two attractions nearby that you can check out.
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.
Northside District
If you're spending some time in Northside District, Lexington Opera House and West Sixth Brewing are top sights worth seeing.
Kenwick
While Kenwick isn't home to many top sights, Ashland Henry Clay Estate and Lexington Memorial Coliseum are some notable places to visit nearby.
Downtown Lexington
While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.
Historic South Hill
While Historic South Hill might 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.
