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
Lexington featuring tranquil scenes and farmland

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

Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$202 per night from 29 Nov to 30 Nov
S$202
29 Nov - 30 Nov
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
Clean. Nice and comfortable Rooms. Friendly staff.

Reviewed on 10 Nov, 2025

Hyatt Regency Lexington
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$250 per night from 28 Nov to 29 Nov
S$250
28 Nov - 29 Nov
includes taxes & fees
9.4/10 Exceptional! (1,045 reviews)
We had a wonderful stay. The hotel was beautiful. The room was well decorated, and the bedding was comfortable. We loved the lounge and the service was excellent. We will definitely return.

Reviewed on 14 Nov, 2025

The Manchester
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$89 per night from 30 Nov to 1 Dec
S$89
30 Nov - 1 Dec
includes taxes & fees
8.2/10 Very Good! (1,458 reviews)
Lisa was great!

Reviewed on 15 Nov, 2025

GuestHouse Lexington
See all 836 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

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

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$55
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

S$64
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Makers Mark, Four Roses or Woodford Reserve or Bulleit or Others

Groups: Makers Mark OR Buffalo Trace OR Woodford or Others

S$234
per adult
Groups: Makers Mark OR Buffalo Trace OR Woodford or Others
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.