Cumberland Hill Holidays

Book a Hotel + Flight or Car together to unlock savings

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 4.185.460 ₫ per night from 8 Mar to 9 Mar
4.185.460 ₫
5.310.132 ₫ total
8 Mar - 9 Mar
includes taxes & fees
9.4/10 Exceptional! (1,149 reviews)
Clean rooms, friendly staff, and good restaurants. I especially like the music selections played through the hotel.

Reviewed on 30 Jan 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 2.887.419 ₫ per night from 22 Feb to 23 Feb
2.887.419 ₫
3.351.427 ₫ total
22 Feb - 23 Feb
includes taxes & fees
8.6/10 Excellent! (1,004 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 3.739.104 ₫ per night from 16 Feb to 17 Feb
3.739.104 ₫
4.339.978 ₫ total
16 Feb - 17 Feb
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Nice hotel but looks outdated.

Reviewed on 2 Feb 2026

Hyatt Regency Lexington
See all 854 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 1null000null000 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

It's beginning to look a lot like Christmas.

Fayette Mall

You can do some window-shopping at Fayette Mall during your trip to Lexington. Discover the area's acclaimed theatre scene or seek out its horse riding.

Fayette Mall
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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
Messing around this morning

Eastern Kentucky University

Enjoy the student vibe when you visit Eastern Kentucky University during your travels in Richmond. While in this family-friendly area, you can savour the top-notch restaurants.

Eastern Kentucky University