Castlewood Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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
Top Holiday Package Deals in Castlewood
Price found within the past 48 hours. Click for updated prices.
Bluegrass Inn
Price was CA $785, price is now CA $755 per person
CA $755
per person
Apr 20 - Apr 25
found 19 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Lexington (LEX)
8/10 Very Good! (1,002 reviews)
Room ok. Had a smell of old ground in smoke like you couldn’t get it out of the sheets or furniture No real cream for breakfast only powdered stuff
Reviewed on Feb 25, 2026
Comfort Inn & Suites Springfield
Price was CA $843, price is now CA $783 per person
CA $783
per person
Apr 20 - Apr 25
found 19 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Lexington (LEX)
6.6/10 (101 reviews)
The room was very clean and comfortable. The decor was very nice. The staff was welcoming and friendly. I would stay at this hotel again.
Reviewed on Jan 11, 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
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
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Mar 22 to Mar 23
CA $231
CA $292 total
Mar 22 - Mar 23
includes taxes & fees
9.6/10 Exceptional! (1,178 reviews)
Room was spotless and the tile work was amazing. Nice choices for the mini-bar
Reviewed on Feb 28, 2026
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 Mar 12 to Mar 13
CA $156
CA $181 total
Mar 12 - Mar 13
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Everything was nice.
Reviewed on Feb 23, 2026
Hilton Lexington/Downtown
369 West Vine Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from Mar 8 to Mar 9
CA $206
CA $239 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Of the 4 Hilton's I stay in regularly in KY and TN, this one has room for improvement. Building is very old and was the most luxurious of the downtown hotels. Unfortunately all that was lost during a bad renovation. Property is not a luxury hotel at all. Problems everywhere. Horrible wall paper pealing ...
Reviewed on Feb 28, 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
University of Kentucky
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
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 $81
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
CA $136
per adult
Bites of the Bluegrass Cocktails & Bites Tour
CA $144
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.