A Victorian-style building with a turret and a tree in front.

Highlands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

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

    Plan, book, and manage your trip all in one place

The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 27 - Jan 31

    Cottonwood Airport & Expo Hotel Louisville + Flight

    Shively
    4 nights
    3.5 star property
    8.8/10 - Excellent (1,007 reviews)
    Roundtrip • Montreal (YMQ) - Louisville (SDF)
    YUL - LEX • 1 stop LEX - YUL • 1 stop
    CA $1,156
    CA $977
    per traveller
    found 14 hours ago
    Cottonwood Airport & Expo Hotel Louisville
  • Jan 27 - Jan 31

    Hyatt Regency Louisville + Flight

    Downtown Louisville
    4 nights
    4.0 star property
    8.8/10 - Excellent (1,003 reviews)
    "Housekeeping knocked"
    Reviewed November 8, 2026
    Roundtrip • Montreal (YMQ) - Louisville (SDF)
    YUL - LEX • 1 stop LEX - YUL • 1 stop
    CA $1,582
    CA $1,240
    per traveller
    found 14 hours ago
    Hyatt Regency Louisville
  • Jan 27 - Jan 31

    Hotel Distil, Autograph Collection + Flight

    Downtown Louisville
    4 nights
    4.0 star property
    9.6/10 - Exceptional (519 reviews)
    "Excellent location and room!"
    Reviewed November 6, 2026
    Roundtrip • Montreal (YMQ) - Louisville (SDF)
    YUL - LEX • 1 stop LEX - YUL • 1 stop
    CA $1,910
    CA $1,586
    per traveller
    found 14 hours ago
    Hotel Distil, Autograph Collection
  • Jan 27 - Jan 31

    The Grady + Flight

    Downtown Louisville
    4 nights
    4.0 star property
    9.4/10 - Exceptional (1,009 reviews)
    "Would definitely stay here again."
    Reviewed November 8, 2026
    Roundtrip • Montreal (YMQ) - Louisville (SDF)
    YUL - LEX • 1 stop LEX - YUL • 1 stop
    CA $1,429
    CA $1,219
    per traveller
    found 14 hours ago
    The Grady
  • Jan 27 - Jan 31

    Holiday Inn Express Louisville Airport Expo Center by IHG + Flight

    Hayfield Dundee
    4 nights
    2.5 star property
    8.6/10 - Excellent (1,007 reviews)
    "Check in was great and fast.The room was nice and clean.The breakfast was above average.Also my daughter flew in from Houston and the staff picked her up with the shuttle from the airport with no problem"
    Reviewed November 8, 2026
    Roundtrip • Montreal (YMQ) - Louisville (SDF)
    YUL - LEX • 1 stop LEX - YUL • 1 stop
    CA $1,141
    CA $987
    per traveller
    found 14 hours ago
    Holiday Inn Express Louisville Airport Expo Center by IHG

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most.

Downtown Louisville

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.

St. Matthews

Major shopping destination with the fifth-largest mall in Kentucky, Mall St. Matthews, and smaller centers along Shelbyville Road. Don't miss the historic St. Matthew's Episcopal Church and Holy Trinity.

Old Louisville

Boasting Victorian architecture and the highest concentration of stained glass windows in residential homes, Old Louisville offers a walkable neighborhood with pedestrian-only streets, diverse dining options, and attractions like Central Park and the Conrad-Caldwell House.

Fairgrounds

While visiting Fairgrounds, you might make a stop by sights like Freedom Hall and Kentucky Kingdom.

Jeffersontown

Jeffersontown is known for its abundant dining options, and you can plan a trip to Jeffersontown Commons Shopping Center and Bluegrass Indoor Karting while you're in town.

What to do near Highlands

Highlands Hotel Deals

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 Highlands vacation package cost?

Cross off another part of the world with our Highlands vacation packages, which start from a low CA $977. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.