Castlewood Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • 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
A parade with people in colorful costumes on a wet street.

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 Explorium.

Find hotels in Downtown Lexington
A parade with people in colorful costumes on a wet street.

Northside District

While visiting Northside District, you might make a stop by sights like Lexington Opera House and West Sixth Brewing.

Find hotels in Northside District
A river with a bridge, a town with historic buildings, and a hilly landscape in the background.

Liberty Area

If you're spending some time in Liberty Area, Hamburg Place and Hamburg Pavilion are top sights worth seeing.

Find hotels in Liberty Area
A grand building with large wooden doors and a sign reading "First Methodist Episcopal Church South."

Historic South Hill

While Historic South Hill may 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.

Find hotels in Historic South Hill
A paved pathway flanked by trees and a wooden fence.

Beaumont Residential

While Beaumont Residential isn't home to many top sights, Kentucky Aviation Museum and Keeneland Racing Course are some notable places to visit nearby.

Find hotels in Beaumont Residential

Top hotels in Castlewood

GuestHouse Lexington

GuestHouse Lexington

2261 Elkhorn Road Lexington KY
Fully refundable
€72
26 Oct - 27 Oct
includes taxes & fees
GuestHouse Lexington
21c Museum Hotel Lexington

21c Museum Hotel Lexington

167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
€138
23 Nov - 24 Nov
includes taxes & fees
21c Museum Hotel Lexington
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
€123
15 Nov - 16 Nov
includes taxes & fees
Marriott Lexington Griffin Gate Golf Resort & Spa
See all 862 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.

Stay near popular Castlewood attractions

Loudoun House

Find out about the history of Lexington when you take a trip to Loudoun House. Make time for the shops and horse riding in this family-friendly area.
See properties

Castlewood Park

Castlewood Park is just one of the places to see in Lexington, so why not enjoy the other things to explore during your travels? Attend a sporting event or visit the shops in this family-friendly area.
See properties

Things to do

Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others

Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others

€196
per adult
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others
Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

€9
per adult
80% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum!
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

€88
per adult
100% of travellers recommend
Lexington: Downtown Walking Food & History Tour
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.