Castlewood Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

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 Explorium.

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

Northside District

If you're spending some time in Northside District, Lexington Opera House and West Sixth Brewing are top sights worth seeing.

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

Liberty Area

1 out of top 10 points of interest in this 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 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.

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

Beaumont Residential

If you're looking for some top things to see and do in Beaumont Residential and surrounding area, you can visit Kentucky Aviation Museum and Keeneland Racing Course.

Find hotels in Beaumont Residential

Castlewood Hotel Deals

GuestHouse Lexington

GuestHouse Lexington

2261 Elkhorn Road Lexington KY
Fully refundable
￥10,630
￥12,339 total
Oct 13 - Oct 14
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
￥21,618
￥25,883 total
Nov 1 - Nov 2
includes taxes & fees
21c Museum Hotel Lexington
The Manchester

The Manchester

941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
￥30,013
￥37,592 total
Nov 1 - Nov 2
includes taxes & fees
The Manchester
See all 841 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 horseback 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

Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

￥1,569
per adult
80% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum!
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

￥15,531
per adult
100% of travellers recommend
Lexington: Downtown Walking Food & History Tour
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others

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

￥34,514
per adult
Bourbon group: 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.