Upcountry Maui Vacation Packages

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Top Upcountry Maui Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Kihei Kai Nani

Kihei Kai Nani

3.5 out of 5
South Kihei
Price was CA $2,203, price is now CA $1,690 per person
CA $1,690
per person
Sep 11 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
10/10 Exceptional! (1 review)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was CA $2,831, price is now CA $1,873 per person
CA $1,873
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8/10 Very good! (373 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 Jun 14, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Price was CA $7,810, price is now CA $5,791 per person
CA $5,791
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
If there isn’t a wedding going on watch the sunset from the front lawn area by the old ice cream truck. Better view than from the birdcage. More open and less blockage. Great high end vibe.

Reviewed on Jun 22, 2026

Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

3.5 out of 5
Price was CA $3,116, price is now CA $2,321 per person
CA $2,321
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Kahului (OGG)
8.6/10 Excellent! (221 reviews)
Includes attendance to classes offered. We had fun. Welcoming staff and teachers

Reviewed on Jun 13, 2026

Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was CA $3,766, price is now CA $2,849 per person
CA $2,849
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8.4/10 Very good! (892 reviews)
Everything is good except for the soft bed

Reviewed on Jun 25, 2026

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Upcountry Maui Hotel Deals

Gods Peace Of Maui

Gods Peace Of Maui

2 out of 5
1290 Haliimaile Rd Makawao HI
The price is CA $236 per night from Jul 5 to Jul 6
CA $236
CA $281 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (124 reviews)
"Our stay at Cottage Peace of Maui was absolutely wonderful! The cottage was clean, comfortable, peaceful, and had everything our family needed for a relaxing vacation. The location was perfect for exploring the island while still enjoying a quiet retreat. A very special thank you to Mika and Tammi ..."

Reviewed on Jun 26, 2026

Gods Peace Of Maui
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 CA $1,341 per night from Jul 11 to Jul 12
CA $1,341
CA $1,685 total
Jul 11 - Jul 12
includes taxes & fees
Four Seasons Resort Maui at Wailea
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 CA $1,020 per night from Jul 21 to Jul 22
CA $1,020
CA $1,293 total
Jul 21 - Jul 22
includes taxes & fees
9.2/10 Wonderful! (1,090 reviews)
"The staff was fantastic. Our room was right next to the elevator so didn’t love that. Lots of the pool wasn’t as clean as it usually is due to people eating and drinking in the pool. Wish that was policed a little more but overall very nice hotel"

Reviewed on Jun 26, 2026

The Westin Maui Resort & Spa, Ka'anapali
See all 13,508 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.
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All Inclusive Vacations
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Stay near popular Upcountry Maui attractions

Haleakala Crater

9.6/5 (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.
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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 travelers to Upcountry Maui during the COVID-19 outbreak?
If it's your first time traveling 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 travelers 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.

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