Castlewood Vacations

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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
A parade with people in colorful costumes on a wet street.

Downtown Lexington

1 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.

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A parade with people in colorful costumes on a wet street.

Northside District

If you're spending some time in Northside District, Lexington Opera House and West Sixth Brewing are top sights worth seeing.

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A river with a bridge, a town with historic buildings, and a hilly landscape in the background.

Liberty Area

If you're spending some time in Liberty Area, Hamburg Place and Hamburg Pavilion are top sights worth seeing.

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A grand building with large wooden doors and a sign reading "First Methodist Episcopal Church South."

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.

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Single white horse grazing at dawn on top of a hill.

Picadome

When in Picadome, you can plan a visit to Kroger Field and Red Mile Racetrack, some noteworthy sights in the nearby area.

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Castlewood Hotel Deals

The Manchester

The Manchester

941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
NT$5,184
NT$6,577 total
Sep 7 - Sep 8
includes taxes & fees
The Manchester
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

1800 Newtown Pike Lexington KY
NT$3,734
NT$4,977 total
Sep 6 - Sep 7
includes taxes & fees
Marriott Lexington Griffin Gate Golf Resort & Spa
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
NT$3,402
NT$3,949 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,021 reviews)
"Very professional and courteous staff. Rooms and hallways quiet which was nice. Got room here twice on a trip driving to and from our destination. Second time of staying here the room did not seem as clean, and again there were no towels at the pool which happened the first stay too, however, the ..."

Reviewed on 2026/8/14

DoubleTree Suites by Hilton Hotel Lexington
See all 865 properties in Castlewood
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.
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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.
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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.