Cumberland Hill Vacation Packages

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Top Holiday Package Deals in Cumberland Hill

Price found within the past 48 hours. Click for updated prices.
Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
9.4/10 Exceptional! (95 reviews)
Absolutely amazing stay.

Reviewed on Jul. 14, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
8.8/10 Excellent! (1,003 reviews)
Lovely hotel and beautiful art/cocktails/info provided However the air con was so cold even though set to 19.5 We couldn’t get it right And the cleaning wasn’t up to a scratch We loved the bar area and the bar man was so friendly An overall good stay

Reviewed on Jul. 24, 2025

The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
9.4/10 Exceptional! (809 reviews)
Beautiful property, shower was amazing, beds are super comfortable!

Reviewed on Jul. 25, 2025

Courtyard Lexington Keeneland/Airport

Courtyard Lexington Keeneland/Airport

3 out of 5
Beaumont Residential
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
8.8/10 Excellent! (747 reviews)
Check out is at noon but housekeeping started knocking at 9am. There should be a system in place so that they know when a guest has checked out.

Reviewed on Jul. 24, 2025

Fairfield Inn & Suites Lexington Keeneland Airport

Fairfield Inn & Suites Lexington Keeneland Airport

2.5 out of 5
Beaumont Residential
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
8.8/10 Excellent! (657 reviews)
Front desk night clerk was extremely helpful! He helped me get a shuttle and parking set up for a very early morning flight. Deeply appreciated and would stay again in a heartbeat.

Reviewed on Jul. 19, 2025

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
Lexington featuring tranquil scenes and farmland

Downtown Lexington

1 out of top 10 points of interest in this area
4/5(1 area review)

While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.

Find hotels in Downtown Lexington

Cumberland Hill Hotel Deals

Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Aug 24 to Aug 25
CA $92
CA $107 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (86 reviews)
"Nice clean bed"

Reviewed on Jul. 23, 2025

Spark by Hilton Lexington Hamburg
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Aug 24 to Aug 25
CA $186
CA $216 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
Amazing hotel
"Our stay was amazing. We were in town for NYAA Cheer Nationals and anything we needed or any questions we had was answered. Staff was very nice and helpful. Location was very convenient as well and we were able to walk across the street for both days of competition. Will definitely stay again."

Reviewed on Jul. 26, 2025

Hilton Lexington/Downtown
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundable
The price is CA $91 per night from Aug 3 to Aug 4
CA $91
CA $106 total
Aug 3 - Aug 4
includes taxes & fees
8/10 Very Good! (1,287 reviews)
Visit
"It was great as always."

Reviewed on Jul. 26, 2025

GuestHouse 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.
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Frequently asked questions

How much does a Cumberland Hill vacation package cost?
Live it up in Cumberland Hill from as little as CA $878. 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 vacation 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 vacation 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 vacation you've always dreamed of in Cumberland Hill is much closer than you thought!
Where should I stay in Cumberland Hill?
Travelers 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 vacation?
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 traveling 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 vacation is only a few clicks away.
Can I choose my airline with a Cumberland Hill Expedia vacation 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 vacation package?
You sure can, and we're here to help. You may be able to amend or cancel your Cumberland Hill vacation 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

University of Kentucky

University of Kentucky

4.5/5(7 reviews)

Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

University of Kentucky
Fayette Mall

Fayette Mall

4.5/5(12 reviews)

You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.

Fayette Mall
Eastern Kentucky University

Eastern Kentucky University

3.5/5(2 reviews)

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

Eastern Kentucky University

Things to do

Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

CA $67
per adult
86% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

CA $135
per adult
Lexington: Downtown Walking Food & History Tour
Distillery District Food & History Tour in Lexington

Distillery District Food & History Tour in Lexington

CA $135
per adult
Distillery District Food & History Tour in Lexington
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.