Castlewood Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Our guide on where to stay in Castlewood
Find the best Castlewood areas and neighborhoods for the activities you enjoy most. Learn more about Castlewood
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.
Our pick of the best Castlewood Hotel Deals
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is AU$323 per night from 31 May to 1 June
AU$323
31 May - 1 June
includes taxes & fees
9.6/10 Exceptional! (1,281 reviews)
Hôtel is beautiful but the staff are very cold
Reviewed on 13 May 2026
Hotel LEX, Trademark Collection by Wyndham
5532 Athens Boonesboro Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 18 May to 19 May
AU$143
18 May - 19 May
includes taxes & fees
8.2/10 Very Good! (701 reviews)
The room was clean, but the lighting in the room was terrible. The rooms appeared newly remodeled but lacked modern lighting. The pool area was very nice, clean and big. Overall it was okay..would I stay there again? No
Reviewed on 14 May 2026
Holiday Inn Express Lexington Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is AU$172 per night from 31 May to 1 June
AU$172
31 May - 1 June
includes taxes & fees
9.4/10 Exceptional! (2,197 reviews)
It is just a little plain and not really updated but nothing bad.
Reviewed on 15 May 2026
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.
Discover the most popular places to visit in Castlewood
Buffalo Trace Distillery
You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while in the area.
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.
The Kentucky Castle
Enjoy a trip to The Kentucky Castle and popular activities such as horse riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Activities
Unique Horse Farm Tours with Insider Access to Private Farms
AU$81
per adult
90% of travellers recommend
From Lexington: Kentucky Horse Farms Tour
AU$81
per adult
100% of travellers recommend
Lexington: Downtown Walking Food & History Tour
AU$137
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.