Castlewood Packages (Flight + Hotel)
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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.
Northside District
While visiting Northside District, you might make a stop by sights like Lexington Opera House and West Sixth Brewing.
Liberty Area
If you're spending some time in Liberty Area, Hamburg Place and Hamburg Pavilion are top sights worth seeing.
Historic South Hill
While Historic South Hill may 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
While there might not be top attractions in Picadome, you can explore the larger area and discover places like Kroger Field and Red Mile Racetrack.
Top hotels in Castlewood
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
฿3,506
฿4,069 total
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (1,036 reviews)
"Great hotel. Great location. Nice pool. Staff was friendly and helpful. Hotel was clean. The only issue I have is that there is a $15 per night parking fee which I wasn't made aware of until I checked in. There really is no reason to charge $15 and night for parking. It's not like somebody is checking ..."
Reviewed on 17 Aug 2026
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
฿5,342
฿6,778 total
7 Sept - 8 Sept
includes taxes & fees
9.6/10 Exceptional! (1,395 reviews)
"Wonderful stay, very relaxed, friendly staff. Rooftop had a young vibe. Bar/lounge in hotel classy."
Reviewed on 16 Aug 2026
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
฿3,420
฿4,633 total
7 Sept - 8 Sept
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
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.
Loudoun House
Find out about the history of Lexington when you take a trip to Loudoun House. Make time for the shops and horse riding in this family-friendly area.
Things to do
Unique Horse Farm Tours with Insider Access to Private Farms
฿1,955
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
฿3,276
per adult
100% of travellers recommend
Bites of the Bluegrass Cocktails & Bites Tour
฿4,137
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.