Upcountry Maui Holidays from NZ$3,189

Book a Hotel + Flight or Car together to unlock savings

Photo by Project Forever

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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 Holiday Deals

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

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was NZ$3,593, price is now NZ$3,189 per person
NZ$3,189
per person
7 Aug - 11 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.4/10 Very Good! (883 reviews)
We arrived at the property on June 10th. Upon entering the property, we noticed that the apartment was a bit run down. The Sofas didn't look clean. In addition, we found cockroaches in front of bedroom, in the bathroom, kitchen, and the ceiling in the living room area. This kind of humper my stay because I have an issue with cockroaches and cleanliness. I spent a good amount of time in the balcony, which was fairly clean and relaxing. I mentioned the roaches to the main office, and the attendant offered something to kill the roaches, but it was not advisable for our own health, so I declined.

Reviewed on 18 June 2026

Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was NZ$3,757, price is now NZ$3,306 per person
NZ$3,306
per person
7 Aug - 11 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8/10 Very Good! (372 reviews)
Staff was nice, I did find cockroaches in my room. When I told the staff they asked me what I wanted them to do about it.... other than that there is a nice full kitchen and an easy walk to the BEACH.

Reviewed on 14 June 2026

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
South Kihei
Price was NZ$5,050, price is now NZ$4,481 per person
NZ$4,481
per person
7 Aug - 11 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9/10 Wonderful! (1,014 reviews)
Perfect stay. Staff was friendly. Absolutely perfect location on the island. Highly recommend

Reviewed on 13 June 2026

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
Wailea
Price was NZ$5,833, price is now NZ$5,212 per person
NZ$5,212
per person
7 Aug - 11 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9.2/10 Wonderful! (1,000 reviews)
This was a nice resort. Probably a little more costly than it should be. Beautiful ocean view. No direct beach access which was kind of a bummer. Game room, Movie Room, Gym, Spa were all nice to haves. Bars by the pools, but not swim up. No real main bar other than in the restaurant…

Reviewed on 19 June 2026

Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

3.5 out of 5
Price was NZ$3,748, price is now NZ$3,388 per person
NZ$3,388
per person
7 Aug - 11 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.6/10 Excellent! (220 reviews)
Includes attendance to classes offered. We had fun. Welcoming staff and teachers

Reviewed on 13 June 2026

Upcountry Maui Holiday

Our pick of the best Upcountry Maui Hotel Deals

Gods Peace Of Maui

Gods Peace Of Maui

2 out of 5
1290 Haliimaile Rd Makawao HI
The price is NZ$343 per night from 22 June to 23 June
NZ$343
22 June - 23 June
includes taxes & fees
8.8/10 Excellent! (120 reviews)
"One of the best places I’ve been at! If you’re looking for"

Reviewed on 15 June 2026

Gods Peace Of Maui
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4.5 out of 5
2365 Kaanapali Pkwy Lahaina HI
Fully refundableReserve now, pay when you stay
The price is NZ$1,583 per night from 19 July to 20 July
NZ$1,583
19 July - 20 July
includes taxes & fees
9.2/10 Wonderful! (1,069 reviews)
"Amazing time! The property was in a great area and had many things to do for the little ones as well as an adult only area."

Reviewed on 19 June 2026

The Westin Maui Resort & Spa, Ka'anapali
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 NZ$1,758 per night from 8 July to 9 July
NZ$1,758
8 July - 9 July
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"It’s got an amazing location. It felt like they are letting the hotel go down a bit though. The staff serving the pool area was paper thin. Cabana rentals that use to be $500 are now $1700/day. Our room had a broken ceiling light we had to have a repair man do for over a hour and even after that ..."

Reviewed on 15 June 2026

Grand Wailea Maui, A Waldorf Astoria Resort
See all 13,525 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.

Discover the most popular places to visit in Upcountry Maui

Haleakala Crater

Haleakala Crater

5/5(7 reviews)

The birthplace of the island of Maui offers stunning views and inspiring landscapes.

Haleakala Crater

Haleakalā Visitor Center

Explore the lovely green spaces of Haleakalā Visitor Center and enjoy the golf courses in Kula. Wander through the beautiful beaches and seaside in this relaxing area.

Haleakalā Visitor Center

Kalahaku Overlook

Explore the great outdoors at Kalahaku Overlook, a lovely green space in Kula. Wander the beaches in this relaxing area.

Kalahaku Overlook

Frequently asked questions

Can I cancel my flight booking to Upcountry Maui due to COVID-19?
Our handy Customer Service Portal is your one-stop shop for most travel queries, including about flight changes related to COVID-19. For greater peace of mind, read through the terms and conditions of your airfare before booking your tickets.
What's the best way to find cheap flights to Upcountry Maui that have flexible change policies?
We understand that travel schedules can change in a flash, so reserving a flexible fare with Expedia makes good sense. Tick the "No change fee" box under the "Flexible change policies" filter. Your low-priced, flexible flight to Upcountry Maui is just a few clicks away.
What are some of the general tips for travellers to Upcountry Maui during the COVID-19 outbreak?
If it's your first time travelling during COVID-19  you'll notice a host of new standards and rules in place. Take note of these tips and make your journey to Upcountry Maui go off without a hitch:
  • Find out if any travel restrictions apply to your destination and origin before booking anything. Also check if there are any special conditions you'll have to follow on arrival, such as health testing.
  • When you pass through airport screening, keep your face mask on. You will be asked to lower it briefly for identification purposes. Passengers who refuse to wear a mask may be fined and denied entry.
  • To reduce the potential of cross-contamination, place your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA employee.
  • You're permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on bag. You'll have to remove it for X-ray scanning.
  • Empty your personal items from your pockets, like your wallet, coins and keys, and put them in your carry-on instead of into bins. This will reduce handling during the screening process.
  • If you're taking food through the security checkpoint, put it in a clear plastic bag and then into a screening bin. This reduces the likelihood that a TSA employee will need to touch your food container or carry-on bag for closer inspection.

Which airlines fly to Upcountry Maui?
Arrange your airfare with Hawaiian Airlines and start working on your Upcountry Maui travel itinerary. This well-known airline offers 1202 flights every month to Kahului Airport (OGG), a main gateway.
How can I find cheap tickets to Upcountry Maui?
To pick up an awesome deal to Upcountry Maui, book well ahead. Also use Expedia's handy "flexible dates" feature at the top of your search results. This will compare the cheapest prices for similar time frames. In the last seven days, was the best price for a flight to Upcountry Maui.
How much is a flight to Upcountry Maui?
In the last seven days, round-trip flights to Upcountry Maui sold for as little as and peaked at . For one-way trips out of (), the lowest amount paid during this same period was just .
What are the most popular airports to fly into in Upcountry Maui?
Upcountry Maui's main airport is Kahului Airport (OGG). Get your amazing journey underway by securing a fare on one of the 3826 flights every month to this destination.
When is the cheapest time to fly to Upcountry Maui?
Leave earlier in the week to book a bargain airfare to Upcountry Maui. Tuesday is normally the most economical day to fly, with Monday running a close second. Saturday typically has the highest ticket prices. This is because many travellers like to start their trip on a weekend.
How much is a plane ticket to Upcountry Maui?
In the last seven days, seats ranged between and . Swipe through our awesome deals to Upcountry Maui, make a booking and then get ready for your getaway!
Which airlines with flights to Upcountry Maui employ COVID-19 cleanliness policies?
While flying during the COVID-19 pandemic can be nerve-wracking, airlines are doing their bit to ensure the well-being of all on board. These are a few carriers that have introduced changes:
  • Hawaiian Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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.