Cumberland Hill Holidays

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Your Cumberland Hill Holiday

Take the hassle out of planning your next escape by booking a Cumberland Hill holiday package. Immerse yourself in the sights and sounds of this wonderful neighbourhood and enjoy everything it has to offer. Get your trip to Cumberland Hill off to a good start by checking out some of its nearby attractions, such as Fayette Mall and Waveland State Historical Site. Whatever your travel plans or budget, booking the ultimate Cumberland Hill holiday is simple with Expedia.

Our guide on 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

Our pick of the best Cumberland Hill Hotel Deals

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is AU$302 per night from 22 Mar to 23 Mar
AU$302
22 Mar - 23 Mar
includes taxes & fees
9.4/10 Exceptional! (1,166 reviews)
Friendly staff great room wonderful ambience lovely restaurant.. great valet all round an amazing stay..,Thanks Manchester

Reviewed on 15 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 AU$194 per night from 15 Mar to 16 Mar
AU$194
15 Mar - 16 Mar
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
Room was clean front desk staff was great - breakfast was a tad weird as they don’t explain it to you and also wish it was free bar was good bar tender is was a bit quiet and not interactive but overall good stay 8/10

Reviewed on 16 Feb 2026

DoubleTree Suites by Hilton Hotel Lexington
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street Lexington KY
The price is AU$246 per night from 8 Mar to 9 Mar
AU$246
8 Mar - 9 Mar
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Yes everything was good!

Reviewed on 20 Feb 2026

Hilton Lexington/Downtown
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.

Discover the most popular places to visit in Cumberland Hill

The bottling line for the special single barrel Blantons Bourbon.

Buffalo Trace Distillery

You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while in the area.

Buffalo Trace Distillery
Aerial photograph of the Lexington, Kentucky skyline at night with the city alite.

Rupp Arena

Catch an event at Rupp Arena and enjoy other activities in Lexington such as horse riding.Attend a sporting event or simply enjoy the lively bars while you're in the area.

Rupp Arena
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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

Activities

Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

AU$85
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Bites of the Bluegrass Cocktails & Bites Tour

Bites of the Bluegrass Cocktails & Bites Tour

AU$150
per adult
Bites of the Bluegrass Cocktails & Bites Tour
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

AU$143
per adult
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.