Find 5 Star Hotels in Upcountry Maui, HI from ¥24,505

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Check availability on Upcountry Maui 5 Star Hotels

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Compare Upcountry Maui 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1000)
"A good hotel. The free upgrade was nice though I suspect because they weren’t filled. The beach was somewhat mediocre for the price, you’re better off in the North near Kaanapali. The breakfast involved a lot of waiting for someone who there was no clear reason for him helping. It was a buffet, adding a rate limiting step then having him give me attitude about asking for the check is a bit much. At this price point you can do better (look nextdoor)."
The price is ¥99,222
¥117,045 total
includes taxes & fees
May 2 - May 3
Four Seasons Resort Maui at Wailea

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.2 out of 10, Wonderful, (1001)
"Beautiful tropical environment exceptionally maintained. Dining options didn't vary much and were overpriced for value. Warm vs. hot dishes, very small portions. Very friendly staff. "
The price is ¥126,525
¥156,992 total
includes taxes & fees
Apr 23 - Apr 24
The Ritz-Carlton Maui, Kapalua

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
9.0 out of 10, Wonderful, (1001)
"loved it lots of families tho"
The price is ¥119,488
¥148,692 total
includes taxes & fees
May 2 - May 3
Grand Wailea Maui, A Waldorf Astoria Resort

Hotel Wailea, Relais & Chateaux - Adults Only

5.0 star property
9.4 out of 10, Exceptional, (1001)
"Peaceful and beautiful "
The price is ¥126,525
¥157,554 total
includes taxes & fees
Apr 26 - Apr 27
Hotel Wailea, Relais & Chateaux - Adults Only

Montage Kapalua Bay

5.0 star property
9.6 out of 10, Exceptional, (198)
"I liked everything except the dining service. The staff was unfriendly and rude. They should not work there.- they kept us in the bar in excess of 15 minutes even after 4 tables had been open We had to walk over to tell them that tables had been open. "
The price is ¥146,370
¥182,576 total
includes taxes & fees
May 12 - May 13
Montage Kapalua Bay

Ho‘olei Villas at Grand Wailea

5.0 star property
9.6 out of 10, Exceptional, (41)
"Best property in Maui "
The price is ¥259,192
¥314,880 total
includes taxes & fees
May 12 - May 13
Ho‘olei Villas at Grand Wailea

Fairmont Kea Lani Maui Villa Experience

5.0 star property
9.6 out of 10, Exceptional, (5)
"It’s a decent hotel to stay for the family."
Fairmont Kea Lani Maui Villa Experience

Wailea Luxury Hilltop Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (2)
"We loved staying here! The property is lovely and the lanai was perfect for sunsets. It has everything you need and you can walk anywhere you need to go. Will be back! "
Wailea Luxury Hilltop Resort Vistas

Oceanfront Kihei Paradise Vistas

5.0 star property
10.0 out of 10, Exceptional, (1)
Oceanfront Kihei Paradise Vistas
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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.

Learn more about Upcountry Maui

Head to sights like Haleakala Crater and Maui Agricultural Research Center as you discover Upcountry Maui—a relaxing area also known for its island views.

Maui Island featuring landscape views

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Upcountry Maui?
The amount you pay for a 5-star hotel in Upcountry Maui can vary according to when you decide to travel and how long you plan to stay, among a number of factors. Use our price per night filter and other search tools to find the best rate on a plush stay.

  • Search for the lowest price per night from ¥24,505

What makes a hotel 5 stars in Upcountry Maui?
Faultless guest service is at the heart of every 5-star hotel in Upcountry Maui. From the minute you step through the door, staff are at your beck and call, whether arranging valet parking or providing a nightly turn-down service. In addition, hotels have to feature top-rate conveniences to qualify for a 5-star rating. These can include luxury baths, spas or saunas, swimming pools, gastronomic restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Upcountry Maui?
Use Expedia’s filters to find a high-end retreat in Upcountry Maui where everything you need is included. After your initial search, narrow down your results for properties that have 5 stars and are deemed “All inclusive.” The main thing on the agenda at these stays? Pure relaxation and indulgence.
Are there any 5-star vacation rentals in Upcountry Maui?
Although you won’t find any 5-star vacation rentals in Upcountry Maui on our site, we have a range of retreats that promise an unforgettable getaway. Discover one that suits your needs by checking out our vacation rentals in Upcountry Maui.