Castlewood Holidays

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Where to stay in Castlewood

Find the best Castlewood areas and neighborhoods for the activities you enjoy most. Learn more about Castlewood
Downtown Lexington

Downtown Lexington

2 out of top 10 points of interest in this area

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

Find hotels in Downtown Lexington

Top hotels in Castlewood

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is S$132 per night from 3 Jul to 4 Jul
S$132
3 Jul - 4 Jul
includes taxes & fees
9.4/10 Exceptional! (2,198 reviews)
"Breakfast was one of th le best hotel breakfast I have ever had!"

Reviewed on 2 Jun, 2026

Holiday Inn Express Lexington Horse Park Area by IHG
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
100 Canebrake Drive Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$134 per night from 16 Jun to 17 Jun
S$134
16 Jun - 17 Jun
includes taxes & fees
8.8/10 Excellent! (1,162 reviews)
"Comfortable, quick check in, clean hotel"

Reviewed on 2 Jun, 2026

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$271 per night from 21 Jun to 22 Jun
S$271
21 Jun - 22 Jun
includes taxes & fees
9.6/10 Exceptional! (1,306 reviews)
"This hotel was very nice, the upscale restaurants and rooms were very nice."

Reviewed on 2 Jun, 2026

The Manchester
See all 853 properties in Castlewood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Horse barn in Kentucky

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.

Keeneland Racing Course
Aerial photograph of the Lexington, Kentucky skyline at night with the city alite.

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.

Rupp Arena

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
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
See all activities in Lexington

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