Castlewood Vacations from $395
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The Latest Castlewood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Hotel Lexington
per person
Aug 23 - Aug 26
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
8.6/10 Excellent! (1,008 reviews)
Top tier hotel to stay in. 10/10 would recommend, and I most definitely will be staying again.
Reviewed on Jul 6, 2025
The Manchester
Distillery District
per person
Aug 23 - Aug 26
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
9.6/10 Exceptional! (906 reviews)
Fantastic property! The best hotel I’ve stayed at this year. The room was clean. The decor was fantastic. Bed was comfy. Loved the rooftop bar. And the restaurant is in the distillery district so super close to great restaurants, shops and bourbon. We will go back!
Reviewed on Jul 10, 2025
The Sire Hotel Lexington, Tapestry Collection by Hilton
Downtown Lexington
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Lexington (LEX)
9.4/10 Exceptional! (809 reviews)
Very nice staff. Room was great. Very clean. Comfortable bed. Definitely would stay here again
Reviewed on Jul 12, 2025
Hyatt Regency Lexington
Downtown Lexington
per person
Aug 23 - Aug 26
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
8.6/10 Excellent! (1,006 reviews)
This property is old and in serious need of updating. The Expedia pictures do not match the property itself. This property was way overpriced for its condition. There was so much dust behind the mirror in the bathroom I actually saw a dust bunny fall.
Reviewed on Jul 11, 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
Spark by Hilton Lexington Hamburg
2381 Buena Vista Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $78 total per night from Jul 25 to Jul 26
$78 total
Jul 25 - Jul 26
Total includes taxes and fees
8.8/10 Excellent! (51 reviews)
Great stay, will be back again
"Nice property, and well cared for. The breakfast offerings may have included a better fruit selection before I came down. That would be the only improvement I would suggest."
Reviewed on Jul 10, 2025
Hilton Lexington/Downtown
369 West Vine Street, Lexington, KY
$152 nightly
The price is $177 total per night from Jul 20 to Jul 21
$177 total
Jul 20 - Jul 21
Total includes taxes and fees
8.4/10 Very Good! (1,004 reviews)
Nice place
"It is a great area to stay. Hotel was clean & undated. All the staff were friendly & professional. My only complaint is that the air conditioning wouldn’t cool enough."
Reviewed on Jul 9, 2025
Quality Inn Lexington -Horse Park
1938 Stanton Way, Bldg A, Lexington, KY
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $80 total per night from Jul 16 to Jul 17
$80 total
Jul 16 - Jul 17
Total includes taxes and fees
8.2/10 Very Good! (1,635 reviews)
"This has been are favorite stop for several years. Friendly, clean, easy on off highway."
Reviewed on Jul 11, 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
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.
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.
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
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
$30
per traveler
Experience Rebecca Ruth Chocolate Tour & Museum!
$10
per adult
Lexington: Downtown Walking Food & History Tour
$99
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.