Upcountry Maui Holidays from NZ$2,606

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 Vista – Maui Condo & Home

Maui Vista – Maui Condo & Home

4 out of 5
South Kihei
Price was NZ$3,200, price is now NZ$2,606 per person
NZ$2,606
per person
15 June - 20 June
found 10 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.6/10 Excellent! (54 reviews)
Everything was great

Reviewed on 1 Feb 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Save 100% on your flight
Price was NZ$7,920, price is now NZ$5,026 per person
NZ$5,026
per person
15 June - 20 June
found 10 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Everything was Amazing!! Will be coming back

Reviewed on 18 Apr 2026

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
Wailea
Save 100% on your flight
Price was NZ$8,042, price is now NZ$5,742 per person
NZ$5,742
per person
15 June - 20 June
found 10 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9.4/10 Exceptional! (1,003 reviews)
Staff were constantly smiling and were engaging and helpful. They were genuine and attentive offering nice personal solutions. Turn down bed service is always a nice treat after a long day and filling dinner.

Reviewed on 1 May 2026

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5 out of 5
Price was NZ$3,982, price is now NZ$3,120 per person
NZ$3,120
per person
15 June - 20 June
found 10 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.6/10 Excellent! (14 reviews)
The property and rooms are very nice. Very lush and beautiful landscaping and easy walk to the beach. The staff are very friendly and helpful. The issues that we had is that the air conditioner in the room was either not working properly, or undersized for the room. We had it set at 68 and it was hot in the room. We tried to turn it down to 66 and eventually 64, and I have a temp meter and the room was reading 80 degrees at night. It was very uncomfortable to sleep. We couldn't open the windows because all of the screen were either not there, or bent and it let in mosquitos. That was the biggest hang up to making this trip 5 stars.

Reviewed on 27 Apr 2026

Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas

5 out of 5
Central Kihei
Price was NZ$4,017, price is now NZ$3,412 per person
NZ$3,412
per person
15 June - 20 June
found 10 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
10/10 Exceptional! (2 reviews)

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$431 per night from 4 June to 5 June
NZ$431
4 June - 5 June
includes taxes & fees
8.8/10 Excellent! (107 reviews)
Everything was great!! Kitchen, hot tub, snacks, and amenities were so clean and the owners were some of the nicest people I’ve met!! Will be coming back here again and staying for SURE!! Plus it’s centrally located, so pretty much everything is 30 mins away instead of super long drives!

Reviewed on 21 Apr 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$1,425 per night from 9 May to 10 May
NZ$1,425
9 May - 10 May
includes taxes & fees
9.2/10 Wonderful! (1,012 reviews)
Perfect vacation spot

Reviewed on 4 May 2026

The Westin Maui Resort & Spa, Ka'anapali
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 NZ$1,709 per night from 25 May to 26 May
NZ$1,709
25 May - 26 May
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
Clean room Quite room Kindful staff

Reviewed on 25 Apr 2026

Four Seasons Resort Maui at Wailea
See all 13,472 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.