Castlewood Vacations from $294
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The Latest Castlewood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Lexington Medical District by IHG
South Broadway Park
Price was $356, price is now $308 per person
$308
per person
Jan 14 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Lexington (LEX)
18.4/10 Exceptional! (774 reviews)
Great people and place very well kept up
Reviewed on Nov 19, 2025
The Campbell House Lexington, Curio Collection by Hilton
Price was $392, price is now $340 per person
$340
per person
Jan 14 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Lexington (LEX)
16.4/10 Exceptional! (1,000 reviews)
Staff were great. Room was clean and comfortable. On site restaurant had great options. Welcoming fire going in the foyer fireplace.
Reviewed on Nov 8, 2025
Embassy Suites by Hilton Lexington Green
Price was $462, price is now $404 per person
$404
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
18.8/10 Exceptional! (1,001 reviews)
The check in desk crew was welcoming and helpful. Encountered the same in the restaurant and breakfast bar. Good staff! The hotel is very nice…well decorated throughout and the rooms are spacious. Let’s not forget to mention the breakfast bar…stocked with everything for everyone’s taste. I would definitely stay again
Reviewed on Nov 16, 2025
Where to stay in Castlewood
Find the best Castlewood areas and neighborhoods for the activities you enjoy most. Learn more about Castlewood
Downtown Lexington
1 out of top 10 points of interest in this area
4.5/5(27 area reviews)
While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.
Castlewood Hotel Deals
Hyatt Regency Lexington
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $132 total per night from Nov 29 to Nov 30
$132 total
Nov 29 - Nov 30
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
Very clean
Reviewed on Nov 17, 2025
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $215 total per night from Dec 21 to Dec 22
$215 total
Dec 21 - Dec 22
Total with taxes and 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 Nov 14, 2025
GuestHouse Lexington
2261 Elkhorn Road Lexington KY
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $72 total per night from Nov 27 to Nov 28
$72 total
Nov 27 - Nov 28
Total with taxes and fees
8.2/10 Very Good! (1,458 reviews)
Lisa was great!
Reviewed on Nov 15, 2025
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
University of Kentucky
4.5/5(384 reviews)
Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Kentucky Horse Park
4.5/5(328 reviews)
Experience the exciting worlds of horses and horseracing at this equine theme park with multiple museums in the middle of Kentucky’s horse country.
Fayette Mall
4.5/5(321 reviews)
You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.
Things to do
Bites of the Bluegrass Cocktails & Bites Tour
$105
per adult
Distillery District Food & History Tour in Lexington
$99
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.