Upcountry Maui Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

Photo by Project Forever

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 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

Top hotels in Upcountry Maui

Gods Peace Of Maui

Gods Peace Of Maui

2 out of 5
1290 Haliimaile Rd Makawao HI
The price is ฿5,543 per night from 25 Jul to 26 Jul
฿5,543
฿6,581 total
25 Jul - 26 Jul
includes taxes & fees
8.8/10 Excellent! (128 reviews)
"Great convenient bed and breakfast"

Reviewed on 9 Jul 2026

Gods Peace Of Maui
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
The price is ฿27,305 per night from 30 Jul to 31 Jul
฿27,305
฿34,579 total
30 Jul - 31 Jul
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
"Beautiful property, amazing pools and wonderful service."

Reviewed on 9 Jul 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
The price is ฿38,218 per night from 9 Aug to 10 Aug
฿38,218
฿47,548 total
9 Aug - 10 Aug
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
"Excellent staff and service!"

Reviewed on 8 Jul 2026

Four Seasons Resort Maui at Wailea
See all 13,223 properties in Upcountry Maui
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.

Stay near popular Upcountry Maui attractions

Haleakala Crater

9.6/10 (547 reviews)
One of the best places in the U.S. to watch the sunrise is this impressive centerpiece of Haleakalā National Park, marking the birthplace of the island of Maui.
See properties

Frequently asked questions

How much does an Upcountry Maui holiday package cost?
Perhaps less than you imagined — from a tempting , as a matter of fact! By combining flights, hotels and car rentals into your own custom-made holiday 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 holiday?
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 holiday 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 holiday goals, you're bound to find a package to suit your budget.
Can I choose my airline with an Upcountry Maui Expedia holiday 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 holiday package?
Plans can change suddenly, so yes, you can. You may be able to cancel or amend your Upcountry Maui holiday 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.

Explore a world of travel with Expedia

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