Highlands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was CA $1,803, price is now CA $1,410 per person
CA $1,410
per person
Mar 25 - Mar 29
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Room was spotless. Staff was top notch. Amenities as expected but I did expect a microwave in the room. There wasn't one. 9/10 experience. Will definitely book again!

Reviewed on Jan 16, 2026

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $2,834, price is now CA $1,999 per person
CA $1,999
per person
May 19 - May 22
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Louisville (SDF)
8.8/10 Excellent! (1,005 reviews)
Very clean room, the staff was friendly as well. Looking forward to our stay again next year.

Reviewed on Feb 7, 2026

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
Price was CA $5,910, price is now CA $4,520 per person
CA $4,520
per person
Apr 28 - May 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
9.4/10 Exceptional! (1,606 reviews)
Big comfy and clean Fabulouse staff A special shout out to Chad at the bourbon bar for the wonderful conversation

Reviewed on Feb 20, 2026

The Bellwether Hotel

The Bellwether Hotel

3.5 out of 5
Tyler Park
Price was CA $6,022, price is now CA $4,891 per person
CA $4,891
per person
Apr 28 - May 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
8.6/10 Excellent! (31 reviews)
The coldest hotel room I’ve ever stayed in! We stayed in “The Olmstead” in January and maxing out the heater couldn’t quite make it a comfortable temperature in the room - I don’t think it got warmer than 65 in there. I think it’s a combo of the concrete floors and walls with high ceilings and one small unit placed near the ceiling. Otherwise a great room! But I wouldn’t stay there when it’s cold outside again.

Reviewed on Jan 4, 2026

Studio 6 Suites Louisville, KY – Airport/Expo Center

Studio 6 Suites Louisville, KY – Airport/Expo Center

2 out of 5
Highland Park
Price was CA $2,410, price is now CA $1,958 per person
CA $1,958
per person
Apr 28 - May 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
7.2/10 Good! (490 reviews)
Clean room. Friendly staff

Reviewed on Feb 16, 2026

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Landscape of Louisville

Downtown Louisville

4 out of top 10 points of interest in this area
4/5(37 area reviews)

Explore "Museum Row" in the West Main District, catch a game at Louisville Slugger Field, or stroll across the pedestrian-only Big Four Bridge. Enjoy diverse attractions, restaurants, and the Louie Link skywalk.

Find hotels in Downtown Louisville

Highlands Hotel Deals

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Mar 22 to Mar 23
CA $203
CA $239 total
Mar 22 - Mar 23
includes taxes & fees
8.8/10 Excellent! (4,081 reviews)
The room was clean, and well-appointed a wonderful view.

Reviewed on Feb 19, 2026

Galt House Hotel Trademark Collection by Wyndham
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
830 Phillips Lane Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Feb 28 to Mar 1
CA $137
CA $161 total
Feb 28 - Mar 1
includes taxes & fees
8.8/10 Excellent! (1,165 reviews)
Shannon at the front desk was amazing for a last-minute, late-night reservation. 5-Star service.

Reviewed on Feb 20, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $273 per night from Mar 22 to Mar 23
CA $273
CA $321 total
Mar 22 - Mar 23
includes taxes & fees
9.2/10 Wonderful! (1,773 reviews)
Friendly staff, clean rooms, good food options

Reviewed on Feb 16, 2026

Omni Louisville Hotel
See all 2,107 properties in Highlands
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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Highlands vacation package cost?
Cross off another part of the world with our Highlands vacation packages, which start from a low CA $1,410. Select the flights and hotels that suit your style. Then, add on one or two experiences or tours to cap off your unique getaway.
How do I get a cheap travel package to Highlands?
It's as simple as bundling. Hotels, flights and rental cars — combine whatever you need into a Highlands vacation package to save tons of cash. Score even more bargains when you include extras such as day tours to your booking. But that's not the only good part. You have the freedom to customize your vacation your way. We offer more than 550 partner airlines and 1,000,000 hotel options worldwide, so that everyone has a chance to travel and fulfill those vacation dreams.
How far in advance should I book my Highlands vacation?
It all depends on the air carrier, but it's usually possible to look up international airfares on Expedia nearly a year in advance. While it's a good idea to book ahead of time, lucky travelers will occasionally nab a cheaper ticket just weeks before the date of departure.
What does an Expedia Highlands travel package include?
It depends on what kind of trip you have in the works. Highlands vacation deals can include hotels, car rentals and flights. You can mix and match to create the package that suits your budget and style. You can also add on activities and experiences after you've booked to get even bigger discounts.
What should I know before booking a Highlands travel package?
You can save a tidy sum by combining your hotels, flights and rental cars. Once you've created your package, you can add on things like sightseeing tours or experiences. Your next unforgettable vacation is only a few clicks away.
Can I choose my airline with a Highlands Expedia vacation package?
Yes, you sure can. We offer more than 550 partner airlines all over the world, so choose the carrier that matches your travel preferences.
If I'm not able to travel, can I cancel my Highlands vacation package?
It's good to know that you can cancel your Highlands booking if your travel plans have changed. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Discover the most popular places to visit in Highlands

Ky Derby festival balloon glow.

Kentucky Exposition Center

4.5/5(14 reviews)

During your trip, find out what's happening at Kentucky Exposition Center, a top convention center in Louisville. Experience the area's lively festivals and acclaimed art scene.

Kentucky Exposition Center
Churchill Downs showing land animals and horse riding as well as a small group of people

Churchill Downs

4.5/5(22 reviews)

Find more than mint juleps to enjoy at this iconic racetrack, best known as the annual host of the Kentucky Derby.

Churchill Downs
Panorama Ohio River waterway riverboats and bridges leading to heart of downtown Louisville KY

KFC Yum Center

4.5/5(4 reviews)

Catch an event at KFC Yum Center during your trip to Louisville. Stroll along the riverfront or attend a sporting event in the area.

KFC Yum Center

Things to do

Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

CA $13
per adult
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour
Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories

Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories

CA $20
per traveller
Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories
Louisville: NuLu District Food and History Tour

Louisville: 3-Hour Food and History Tour of NuLu District

CA $176
per adult
90% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
See all activities in Louisville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.