Upcountry Maui Vacations from ￥126,166

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The Latest Upcountry Maui Vacation Packages

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
Save 100% on your flight
Price was ￥220,848, price is now ￥126,166 per person
￥126,166
per person
Mar 2 - Mar 7
found 16 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.2/10 Very Good! (814 reviews)
Very clean, great staff. Pool was nice, good location. Living room furniture uncomfortable.

Reviewed on Jan 16, 2026

Kahana Villa

Kahana Villa

3 out of 5
Price was ￥250,974, price is now ￥129,834 per person
￥129,834
per person
Mar 2 - Mar 7
found 16 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8/10 Very Good! (351 reviews)
This place was absolutely amazing! The location was fantasic, the view was beautiful and the two bedroom villa far exceeded my expectations! I will be back and I know exactly where I want to stay!

Reviewed on Jan 6, 2026

Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was ￥263,992, price is now ￥138,429 per person
￥138,429
per person
Mar 2 - Mar 7
found 16 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8/10 Very Good! (351 reviews)
Bed was uncomfortable.

Reviewed on Jan 11, 2026

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
South Kihei
Save 100% on your flight
Price was ￥432,549, price is now ￥232,673 per person
￥232,673
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Kahului (OGG)
8.8/10 Excellent! (1,002 reviews)
The good: Beach is amazing including the snorkeling. Store has everything you need, a little more expensive but not ridiculous. The bad: weird check-in and service. The rooms are obviously managed by different companies. Front desk isn't necessarily your main contact. They call someone else. The 'B' rooms are tiny......only enough room to sleep. No ice....have to buy it for $5 per bag at the store. Overall, we'd come back to this area but not sure if we would do the 'B' room.

Reviewed on Jan 10, 2026

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was ￥312,194, price is now ￥175,138 per person
￥175,138
per person
Mar 2 - Mar 7
found 16 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9/10 Wonderful! (1,465 reviews)
All the staff was super friendly and helpful. The propert was immaculate and very easy access to the beach!

Reviewed on Jan 16, 2026

Find the Best Upcountry Maui Vacation Packages

Upcountry Maui Hotel Deals

Gods Peace Of Maui

Gods Peace Of Maui

2 out of 5
1290 Haliimaile Rd Makawao HI
The price is ￥29,252 per night from Jan 21 to Jan 22
￥29,252
￥34,727 total
Jan 21 - Jan 22
includes taxes & fees
8.8/10 Excellent! (60 reviews)
Room was very clean. Shared spaces were well kept. A little loud after quiet hours but who isn’t?

Reviewed on Jan 10, 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 ￥77,321 per night from Feb 8 to Feb 9
￥77,321
￥100,929 total
Feb 8 - Feb 9
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
Our stay was great

Reviewed on Jan 12, 2026

The Westin Maui Resort & Spa, Ka'anapali
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
2780 Kekaa Dr Lahaina HI
Fully refundableReserve now, pay when you stay
The price is ￥46,392 per night from Feb 11 to Feb 12
￥46,392
￥63,466 total
Feb 11 - Feb 12
includes taxes & fees
8.4/10 Very Good! (1,638 reviews)
The bads: Long line at check in. Low water pressure and screeching in the shower. The goods: the ambiance of The Branch. The friendliness of the people. The room quality. The luau. For the cost a definite good deal.

Reviewed on Jan 12, 2026

Royal Lahaina Resort & Bungalows
See all 13,477 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 featuring tranquil scenes, landscape views and mountains

Haleakala Crater

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.

Haleakala Crater

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.