A barren volcanic landscape with rugged terrain and distant mountains.
Photo by Project Forever
Open Photo by Project Forever

Upcountry Maui 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 Upcountry Maui Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 11 - Dec 13

    Castle at Maui Banyan + Flight

    South Kihei
    2 nights
    3.5 star property
    7.8/10 - Good (309 reviews)
    "All good but our cheap jazz got the small room with two beds and it was small room for sure"
    Reviewed November 6, 2026
    Roundtrip • Vancouver (YVR) - Maui (OGG)
    YXX - OGG • 1 stop OGG - YXX • 1 stop
    CA $2,551
    CA $1,110
    per traveller
    found 1 day ago
    Castle at Maui Banyan
  • Jan 22 - Jan 25

    Hotel Wailea Maui + Flight

    Wailea
    3 nights
    5.0 star property
    9.4/10 - Exceptional (1,004 reviews)
    Roundtrip • Edmonton (YEG) - Maui (OGG)
    YEG - OGG • 1 stop OGG - YEG • 1 stop
    CA $3,627
    CA $2,430
    per traveller
    found 1 day ago
    Hotel Wailea Maui
  • Jan 22 - Jan 25

    Fairmont Kea Lani Maui + Flight

    Wailea
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,005 reviews)
    "Please don’t force me to make a review."
    Reviewed November 9, 2026
    Roundtrip • Edmonton (YEG) - Maui (OGG)
    YEG - OGG • 1 stop OGG - YEG • 1 stop
    CA $4,083
    CA $2,793
    per traveller
    found 1 day ago
    Fairmont Kea Lani Maui
  • Jan 20 - Jan 25

    Grand Champions + Flight

    Wailea
    5 nights
    2.5 star property
    9.2/10 - Wonderful (9 reviews)
    "Nothing"
    Reviewed September 30, 2026
    Roundtrip • Toronto (YYZ) - Maui (OGG)
    YYZ - HNL • 2 stops HNL - YYZ • 1 stop
    CA $3,736
    CA $2,559
    per traveller
    found 1 day ago
    Grand Champions
  • Jan 21 - Jan 26

    Kihei Akahi - Maui Condo & Home + Flight

    South Kihei
    5 nights
    2.5 star property
    7.8/10 - Good (232 reviews)
    "AC did not work."
    Reviewed September 26, 2026
    Roundtrip • Edmonton (YEG) - Maui (OGG)
    YEG - OGG • 1 stop OGG - YEG • 1 stop
    Save 100% on your flight
    CA $3,135
    CA $2,253
    per traveller
    found 12 hours ago
    Kihei Akahi - Maui Condo & Home

Discover the most popular places to visit in Upcountry Maui

Upcountry Maui 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 an Upcountry Maui vacation package cost?

Perhaps less than you imagined — from a tempting CA $1,110, as a matter of fact! By combining flights, hotels and car rentals into your own custom-made vacation package, your getaway to Upcountry Maui is just clicks away.

How do I get a cheap travel package to Upcountry Maui?

One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and rental cars — we've got everything you need. Pick and choose the combination that suits you and watch your savings pile up. We know a travel package is never a one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 hotel options across the globe, which lets you customize your Upcountry Maui adventure.

What are the top hotels in Upcountry Maui?

When it comes to hotels in Spreckelsville, Paia Inn and Kaiholo Hale are two great options. If you're also spending time in Haliimaile, Private Lush 2 Acre Mountain Home Maui Permitted#stmp 2013 and Adorable 1930's Gingerbread House. . . . Permitted look forward to welcoming you.

How far in advance should I book my Upcountry Maui vacation?

It's always wise to book early. Air carriers generally release flight tickets up to a year in advance, and this is a great opportunity to land some rock-bottom prices. Boss just told you to take all your vacation days next week? No need to worry. Expedia are never short on fantastic deals to send you off on the getaway of your dreams, at an affordable price.

What does an Expedia Upcountry Maui travel package include?

With Expedia, you can choose any combination of car rentals, hotels and flights to create your ideal Upcountry Maui travel package. Once you've made your booking, you can add on the fun things like sightseeing tours and activities. Remember, the more you bundle, the bigger the savings!

What should I know before booking an Upcountry Maui travel package?

A travel package can be easier on the wallet than individually booking all you need for your getaway. For example, combine your hotels, flights and rental cars and score impressive savings. No matter your vacation goals, you're bound to find a package to suit your budget.

Can I choose my airline with an Upcountry Maui Expedia vacation package?

Yes, of course. We have more than 550 airline partners all over the world, so pick the carrier that matches your needs.

If I'm not able to travel, can I cancel my Upcountry Maui vacation package?

Plans can change suddenly, so yes, you can. You may be able to cancel or amend your Upcountry Maui vacation package at no cost within 24 hours of booking. For bookings older than that, you can still cancel and rebook, but your car rental company, hotel or airline may charge a fee. Need more information? Have a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

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