Cumberland Hill Holidays

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    Save up to €185 when you book a flight and hotel together*

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Where to stay in Cumberland Hill

Find the best Cumberland Hill areas and neighborhoods for the activities you enjoy most. Learn more about Cumberland Hill
4th of July festival

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.

Find hotels in Downtown Lexington

Top hotels in Cumberland Hill

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is €172 per night from 8 Mar to 9 Mar
€172
8 Mar - 9 Mar
includes taxes & fees
9.4/10 Exceptional! (1,161 reviews)
Friendly and attentive staff. Great location, bar and onsite restaurant.

Reviewed on 9 Feb 2026

The Manchester
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is €109 per night from 22 Feb to 23 Feb
€109
22 Feb - 23 Feb
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Very cool hotel, good amenities, clean, spacious good price really enjoyed it

Reviewed on 2 Feb 2026

DoubleTree Suites by Hilton Hotel Lexington
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
The price is €140 per night from 8 Mar to 9 Mar
€140
8 Mar - 9 Mar
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Fast check in, convenient location, clean

Reviewed on 6 Feb 2026

Hyatt Regency Lexington
See all 859 properties in Cumberland Hill
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.

Frequently asked questions

How much does a Cumberland Hill holiday package cost?
Live it up in Cumberland Hill from as little as . We offer a wonderful selection of hotels, flights and rental cars to suit every budget and style. Land even more discounts when you add some sightseeing activities to your holiday package.
How do I get a cheap travel package to Cumberland Hill?
Bundle your bookings with Expedia to save big on your next big adventure. With more than 550 airlines and 1,000,000 properties globally, your Cumberland Hill holiday package can be customized exactly to suit your budget. With all that extra money, why not throw in some awesome activities and tours? It's an easy way to unlock even more bargains. The holiday you've always dreamed of in Cumberland Hill is much closer than you thought!
Where should I stay in Cumberland Hill?
Travellers come from every corner of the globe to see University of Kentucky and Keeneland Racing Course in Cumberland Hill. Book a room close to these fantastic attractions and visit them whenever you please.
How far in advance should I book my Cumberland Hill holiday?
It all depends on the airline, but it's usually possible to compare international flights on Expedia up to a year in advance. While it's generally recommended to book ahead of time, lucky customers will sometimes score a cheaper ticket just weeks prior to departure dates.
What does an Expedia Cumberland Hill travel package include?
That depends on what you're looking for. If you're travelling alone, you might decide to combine flights and hotels. Bringing the whole crew to Cumberland Hill? A travel package including hotels, flights and rental cars might be a better fit. Expedia gives you the flexibility and freedom to tailor-make your travel package.
What should I know before booking a Cumberland Hill travel package?
Find deals that fit your budget with an Expedia package. Airfares, hotels, rental cars — we have everything you need to plan your escape. You'll save big dollars just for combining your bookings. Whether you're taking off on a winter snow adventure or venturing someplace warm, your dream holiday is only a few clicks away.
Can I choose my airline with a Cumberland Hill Expedia holiday package?
Definitely. Expedia has more than 550 airline partners to pick from worldwide. With so many choices, finding the ideal carrier to fly you to Cumberland Hill will be easy.
If I'm not able to travel, can I cancel my Cumberland Hill holiday package?
You sure can, and we're here to help. You may be able to amend or cancel your Cumberland Hill holiday package for free if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If your travel plans unexpectedly change, browse our Customer Service Portal for further information.

Popular places to visit

Kentucky Horse Park showing land animals

Kentucky Horse Park

4.5/5(5 reviews)

Enjoy a trip to Kentucky Horse Park and popular activities such as horse riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Kentucky Horse Park
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The Kentucky Castle

Enjoy a trip to The Kentucky Castle and popular activities such as horse riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Kentucky Castle

Things to do

Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

€8
per adult
80% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum!
Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

€49
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Experience Rebecca Ruth Chocolate Tour & Museum: Group limit 15

Experience Rebecca Ruth Chocolate Tour & Museum

€8
per adult
Experience Rebecca Ruth Chocolate Tour & Museum
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.