Castlewood Vacation Packages
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Top Holiday Package Deals in Castlewood
Price found within the past 48 hours. Click for updated prices.
GuestHouse Lexington
CA $1,365
per person
Oct 6 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Lexington (LEX)
8.4/10 Very good! (1,653 reviews)
We only stayed overnight. But our toilet didn’t flush properly 🤔 that was our only issue. We let the desk know the next morning👍
Reviewed on Sep 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 Rupp Arena.
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.
Picadome
When in Picadome, you can plan a visit to Kroger Field and Red Mile Racetrack, some noteworthy sights in the nearby area.
Castlewood Hotel Deals
Hyatt Regency Lexington
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
CA $165
CA $192 total
Sep 8 - Sep 9
includes taxes & fees
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
CA $143
CA $194 total
Sep 6 - Sep 7
includes taxes & fees
The Manchester
941 Manchester St Lexington KY
CA $243
CA $306 total
Sep 7 - Sep 8
includes taxes & fees
9.6/10 Exceptional! (1,414 reviews)
"Amazing hotel and staff - highly recommend."
Reviewed on Aug 31, 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
Unique Horse Farm Tours with Insider Access to Private Farms
CA $82
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
CA $137
per adult
100% of travellers recommend
Bites of the Bluegrass Cocktails & Bites Tour
CA $173
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.