Castlewood Vacation Packages
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Top Holiday Package Deals in Castlewood
Price found within the past 48 hours. Click for updated prices.
The Sire Hotel Lexington, Tapestry Collection by Hilton
Downtown Lexington
Price was CA $1,223, price is now CA $967 per person
CA $967
per person
Nov 3 - Nov 6
found 18 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lexington (LEX)
9.4/10 Exceptional! (820 reviews)
Like: The neighborhood and close dining. Breakfast was nice. Staff were awesome! Thank you.
A little bit let down by the "spa shower".
Reviewed on Jul. 29, 2025
21c Museum Hotel Lexington
Downtown Lexington
Price was CA $1,743, price is now CA $1,354 per person
CA $1,354
per person
Oct 10 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.8/10 Excellent! (1,003 reviews)
Amazing staff and beautiful hotel
Reviewed on Aug. 29, 2025
Sleep Inn
Price was CA $1,227, price is now CA $1,030 per person
CA $1,030
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lexington (LEX)
8.2/10 Very Good! (557 reviews)
Preston was very helpful with any and all issues and so was the overnight concierge unfortunately the walls were a little thin but they were able to reach out to the guest next door and it helped and on our last day although the breakfast was great every other day it wasn't ready on time for us to have to leave
Reviewed on Aug. 18, 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(1 area review)
While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.
Castlewood Hotel Deals
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Sep 14 to Sep 15
CA $156
CA $181 total
Sep 14 - Sep 15
includes taxes & fees
Hilton Lexington/Downtown
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Sep 7 to Sep 8
CA $223
CA $259 total
Sep 7 - Sep 8
includes taxes & fees
GuestHouse Lexington
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Sep 14 to Sep 15
CA $87
CA $101 total
Sep 14 - Sep 15
includes taxes & fees
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(7 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(12 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.
The Kentucky Castle
Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Things to do
Unique Horse Farm Tours with Insider Access to Private Farms
CA $67
per adult
88% of travellers recommend
Lexington: Downtown Walking Food & History Tour
CA $136
per adult
Distillery District Food & History Tour in Lexington
CA $136
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.