Castlewood Holidays from £1,146

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The Delegate

The Delegate

£1,146
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
London (LGW) to Lexington (LEX)
9.2/10 Wonderful! (529 reviews)
Superb stay on my third trip to Frankfort. Nice central location within walking distance of restaurants and attractions.

Reviewed on 9 Sept 2026

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

£2,424
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
London (LGW) to Lexington (LEX)
9.4/10 Exceptional! (1,004 reviews)
This is a very nice hotel upon entering. Staff was excellent upon check in. Issue was with the room. The room was so humid and damp. The bedding was so damp it was impossible to sleep. I woke up the following morning and all clothes I brought were now damp. My wallet felt like it had been dropped in water. The other issue was a fridge that doesn’t really cool items. It took almost an entire day to chill our drinks. Messaged front desk. Answer to all the problems was to send engineering to fix. Fridge never fixed. Don’t try to keep any leftovers or you’ll become sick. They dropped the ac to 68 while we were gone. That made matters worse. Complained again the next morning. This time engineering brought a tiny dehumidifier and turned the temp back down to 68. It was already full after 2-3 hours. That was a joke again. We would have to empty this out every 2-3 hours while sleeping. Our attempt worked better. I had to turn on the heat instead. Bear in mind it was 95-100 degree days. Our last night there we also went to the bar. Ordered the Old Fashioned on special. Bartender (Whitney) could make it do to missing items. She suggested making a different version. We were fine with that but lo and behold the bill was $41 bucks instead of $30. This was not a high end drink but most certainly high end price. The room could be cleaner. Under the desk was all sticky and slimy. Shower has broken tiles and water swelling drywall. Asking for compensation.

Reviewed on 8 Sept 2026

Elwood Hotel & Suites

Elwood Hotel & Suites

£1,699
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
London (LGW) to Lexington (LEX)
9.4/10 Exceptional! (1,148 reviews)
Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

Zandale
£1,382
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
London (LGW) to Lexington (LEX)
8.8/10 Excellent! (1,001 reviews)
Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

£1,300
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
London (LGW) to Lexington (LEX)
9/10 Wonderful! (1,005 reviews)

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

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.

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

Northside District

While visiting Northside District, you might make a stop by sights like Lexington Opera House and West Sixth Brewing.

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.

A horse grazing on a grassy field with a leafless tree in the background under a purple sky.

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.

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

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.

Top hotels in Castlewood

Hyatt Regency Lexington

Hyatt Regency Lexington

401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
£116
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (1,019 reviews)
"The hotel can use some maintenance and upgrades as it’s showing some wear and tear but was clean and staff was very nice ! Breakfast and dinner was excellent! We had a great view on 15 th floor"

Reviewed on 8 Sept 2026

Hyatt Regency Lexington
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
£110
20 Sept - 21 Sept
includes taxes & fees
8.4/10 Very good! (838 reviews)
"My sister and I stayed here for a sister weekend. The amenities were great. We could stay on site for everything. The staff was very attentive to our needs."

Reviewed on 8 Sept 2026

Marriott Lexington Griffin Gate Golf Resort & Spa
The Manchester

The Manchester

941 Manchester St Lexington KY
£185
28 Sept - 29 Sept
includes taxes & fees
The Manchester
See all 871 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

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.
See properties

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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Things to do

Picture 1 for Activity Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

£33
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
From Lexington: Kentucky Horse Farms Tour

From Lexington: Kentucky Horse Farms Tour

£43
per adult
100% of travellers recommend
From Lexington: Kentucky Horse Farms Tour
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

£73
per adult
100% of travellers recommend
Lexington: Downtown Walking Food & History Tour
See all activities in Lexington

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.