Cumberland Hill Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
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.
Liberty Area
If you're spending some time in Liberty Area, Hamburg Place and Hamburg Pavilion are top sights worth seeing.
Northside District
While visiting Northside District, you might make a stop by sights like Lexington Opera House and West Sixth Brewing.
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.
Beaumont Residential
While Beaumont Residential isn't home to many top sights, Kentucky Aviation Museum and Keeneland Racing Course are some notable places to visit nearby.
Top hotels in Cumberland Hill
Holiday Inn Express Lexington - Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
€95
27 Sept - 28 Sept
includes taxes & fees
Hyatt Regency Lexington
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
€138
1 Oct - 2 Oct
includes taxes & fees
21c Museum Hotel Lexington
167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
€151
30 Sept - 1 Oct
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Would stay in Louisville next time."
Reviewed on 22 Sept 2026
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.
Things to do
Bourbon group: Makers Mark OR Buffalo Trace OR Woodford or Others
€189
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
€9
per adult
80% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
€51
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.