Castlewood Vacations from $455
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The Latest Castlewood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Clarion Hotel Conference Center Lexington North
$455
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Washington (DCA) to Lexington (LEX)
7.6/10 Good! (1,002 reviews)
I would not stay here again. Lack of options so it did the job but wasn’t as nice as it looks online. Also construction going on and told water would be off in the morning.
Reviewed on Sep 28, 2026
21c Museum Hotel Lexington
Downtown Lexington
$571
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Washington (DCA) to Lexington (LEX)
8.8/10 Excellent! (1,007 reviews)
The restaurant wasn't ready so only room service was offered. They didn't honor my "breakfast included" stat.
But, the property was centrally located for all visiting locations. And walkable to evening restaurants.
Reviewed on Oct 1, 2026
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 Explorium.
Liberty Area
If you're spending some time in Liberty Area, Hamburg Place and Hamburg Pavilion are top sights worth seeing.
Northside District
If you're spending some time in Northside District, Lexington Opera House and West Sixth Brewing are top sights worth seeing.
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.
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.
Castlewood Hotel Deals
Holiday Inn Express Lexington - Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
$103 nightly
$120 total
Nov 2 - Nov 3
Total with taxes and fees
21c Museum Hotel Lexington
167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
$156 nightly
$182 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
"The restaurant wasn't ready so only room service was offered. They didn't honor my "breakfast included" stat. But, the property was centrally located for all visiting locations. And walkable to evening restaurants."
Reviewed on Oct 1, 2026
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
$128 nightly
$149 total
Oct 11 - Oct 12
Total with taxes and fees
8.6/10 Excellent! (858 reviews)
"For the price you pay for the rooms, NOTHING is included, i.e. breakfast."
Reviewed on Oct 1, 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.
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.
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.
Things to do
Bites of the Bluegrass Cocktails & Bites Tour
$125
per adult
100% of travellers recommend
Distillery District Food & History Tour in Lexington
$125
per adult
Woodford Reserve, Castle & Key, and Stitzel Weller Bourbon Tour
$285
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.