Castlewood Holidays

    deals illustration
    Better together
    Save up to S$134 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Where to stay in Castlewood

Find the best Castlewood areas and neighborhoods for the activities you enjoy most. Learn more about Castlewood
Lexington featuring farmland and tranquil scenes

Downtown Lexington

1 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

Elwood Hotel & Suites
Elwood Hotel & Suites
4 out of 5
444 Parkway Drive, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is S$145 per night from 29 Jun to 30 Jun
S$145
29 Jun - 30 Jun
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Very nice and the staff was very nice I would definitely stay again"

Reviewed on 27 Jun, 2025

Elwood Hotel & Suites
Fairfield Inn & Suites by Marriott Lexington North
Fairfield Inn & Suites by Marriott Lexington North
3 out of 5
2100 Hackney Pl, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is S$124 per night from 20 Jul to 21 Jul
S$124
20 Jul - 21 Jul
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"The staff is nice, but the property is somewhat in need of repair. The pool and the hot tub area particularly needs repair and has some repaired water damage and in need of some repairs to the shower faucet etc. Accommodations within the room are just fine and the location is perfect."

Reviewed on 26 Jun, 2025

Fairfield Inn & Suites by Marriott Lexington North
Spark by Hilton Lexington Hamburg
Spark by Hilton Lexington Hamburg
2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is S$94 per night from 5 Jul to 6 Jul
S$94
5 Jul - 6 Jul
includes taxes & fees
8.8/10 Excellent! (31 reviews)
"Rooms were comfortable, clean, and quiet"

Reviewed on 27 Jun, 2025

Spark by Hilton Lexington Hamburg
See all 834 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

Keeneland Racing Course

4.5/5(3 reviews)

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

Rupp Arena

4/5(1 review)

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$54
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

S$39
per traveller
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

S$13
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
See all activities in Lexington

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.