Upcountry Maui Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Project Forever
  • 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

Top Upcountry Maui Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

South Kihei
CA $1,709
per person
Oct 16 - Oct 23
found 19 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8/10 Very good! (385 reviews)
Check in was smooth, Rooms were a lot smaller then when looking to book. Air conditioning did not see to work right. Room fan also did not work right, bed was not as comfortable

Reviewed on Aug 22, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
CA $3,745
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
Maui Beach Vacation Club

Maui Beach Vacation Club

North Kihei
CA $2,414
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8.4/10 Very good! (926 reviews)
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

CA $2,067
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
8.2/10 Very good! (24 reviews)
**ONE OF THE WORST HOTEL MANAGEMENT EXPERIENCES WE'VE HAD** We gave Royal Lahaina every opportunity to address our experience privately and even escalated it to their management company, with no response. We stayed for a week in June 2026 with two rooms. Three days before check-in, the hotel couldn't locate our confirmed reservation. After more than TWO HOURS on the phone, manager Gretchen told me they couldn't accommodate our requests, suggested we "book a better hotel like the Montage or the Ritz," said she was canceling our reservations, and hung up. I had to repeatedly call back to ensure our family still had rooms. Management later told me Gretchen received disciplinary action. We tried contacting Hotel Manager Yvette three times during our stay and left two voicemails. She never contacted us until two days after we left. A brief call with my wife was later characterized as accepting their "final resolution": a $75 beach-chair credit. Even after I emailed a detailed complaint, Yvette never personally responded. The resort itself fell short: housekeeping every other day despite a $45/night resort fee; two beach chairs cost another $75/day and were collected at 5 PM sharp; rude beach staff; and large gaps around our renovated room door that let in light, noise and bugs. After spending thousands on two rooms, fees, food and services, management's lack of ownership was the worst part. Ironically, their original advice was best: **Next time, we'll stay somewhere better.

Reviewed on Aug 21, 2026

Palms at Wailea Maui

Palms at Wailea Maui

Wailea
CA $2,218
per person
Oct 28 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
8.4/10 Very good! (546 reviews)
We had an amazing time. We were close to the shops and beaches. The kids loved the pool and we had a beautiful view of the ocean. We would definitely stay there again.

Reviewed on Aug 12, 2026

Ready to book your vacation to Upcountry Maui?

Choose your dates

Upcountry Maui Hotel Deals

Gods Peace Of Maui

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI
CA $221
CA $262 total
Sep 4 - Sep 5
includes taxes & fees
8.6/10 Excellent! (142 reviews)
"Beautiful grounds. Had a "youth hostle" feel. No frills what so ever and all the rooms shared a bathroom. Nothing in the bedrooms except a bed. Common kitchen area and sitting area. Also lots of religious influence decor, books, and pamphlets. We never saw the owners and didn't feel free just to ..."

Reviewed on Aug 21, 2026

Gods Peace Of Maui
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr Lahaina HI
Fully refundableReserve now, pay when you stay
CA $626
CA $824 total
Aug 27 - Aug 28
includes taxes & fees
Hyatt Regency Maui Resort & Spa
Aston Kaanapali Shores

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy Lahaina HI
Fully refundableReserve now, pay when you stay
CA $288
CA $383 total
Aug 24 - Aug 25
includes taxes & fees
Aston Kaanapali Shores
See all 13,310 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

Maui Agricultural Research Center

Find out about the history of Kula when you spend time at Maui Agricultural Research Center. In the area, take in the great live music and beautiful sunsets.
See properties

Haleakalā Visitor Center

9.0/10 (2 reviews)
Explore the lovely green spaces of Haleakalā Visitor Center and enjoy the golf courses in Kula. Wander the beautiful beaches and seaside in this romantic area.
See properties

Hosmer Grove

Explore the great outdoors at Hosmer Grove, a lovely green space in Kula. Stroll along the seaside in this relaxing area, or seek out the yoga studios.
See properties

Maui Spa Retreat

6.6/10 (4 reviews)
Enjoy a trip to Maui Spa Retreat and popular activities like surfing in Makawao. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.
See properties

Hanawi Natural Forest Reserve

10.0/10 (1 review)
Commune with nature and explore the great outdoors at Hanawi Natural Forest Reserve during your travels in Hana. Discover the sunrises in this romantic area, or seek out the yoga studios.
See properties

Polipoli Spring State Recreation Area

Enjoy the beautiful sunsets and explore Polipoli Spring State Recreation Area, a lovely green space in Kula. Stroll along the seaside in this romantic area, or check out its seafood restaurants.
See properties

Kula Botanical Garden

Enjoy the beautiful sunsets and explore Kula Botanical Garden, a lovely green space in Kula. Stroll along the area's beautiful beaches or experience its great live music.
See properties

Frequently asked questions

How much does an Upcountry Maui vacation package cost?
Perhaps less than you imagined — from a tempting CA $1,709, 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.

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.