Castlewood Vacation Packages
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Top Holiday Package Deals in Castlewood
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Danville, KY
CA $1,165
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Lexington (LEX)
7.4/10 Good! (767 reviews)
Room was dirty. Hotel was dirty. It has really has gone downhill. Bugs in first room. Breakfast was very disappointing.
Reviewed on Oct 13, 2026
Clarion Pointe Harrodsburg-Danville
CA $1,197
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Lexington (LEX)
7.4/10 Good! (630 reviews)
Our stay was one night. The staff at the desk were very nice. Rooms were very clean and the bed was comfortable. The breakfast was ok, coffee was wasn’t real hot.
Reviewed on Oct 15, 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 Explorium.
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.
Beaumont Residential
If you're looking for some top things to see and do in Beaumont Residential and surrounding area, you can visit Kentucky Aviation Museum and Keeneland Racing Course.
Castlewood Hotel Deals
GuestHouse Lexington
2261 Elkhorn Road Lexington KY
Fully refundable
CA $90
CA $105 total
Oct 26 - Oct 27
includes taxes & fees
21c Museum Hotel Lexington
167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
CA $194
CA $232 total
Nov 8 - Nov 9
includes taxes & fees
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
CA $247
CA $311 total
Nov 17 - Nov 18
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.
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 $83
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
CA $138
per adult
100% of travellers recommend
Bites of the Bluegrass Cocktails & Bites Tour
CA $175
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.