5 Stars Hotels in Upcountry Maui: Compare Hotel Prices & Find the Cheapest Upcountry Maui, Hawaii 5 Stars Hotels

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Our top choices for Upcountry Maui 5-star hotels

1. Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

Charli

NT$23,152

NT$29,538 total

includes taxes & fees

Sep 16 - Sep 17

2. The Westin Maui Resort & Spa, Ka'anapali

Kannapali Beach Area

Andrew

NT$19,055

NT$24,450 total

includes taxes & fees

Sep 4 - Sep 5

3. The Ritz-Carlton Maui, Kapalua

Kapalua

TAMIKA

NT$25,679

NT$32,708 total

includes taxes & fees

Oct 4 - Oct 5

4. Wailea Beach Resort - Marriott, Maui

Wailea

Michal

NT$20,474

NT$26,528 total

includes taxes & fees

Oct 4 - Oct 5

Maile Three-Bedroom Presidential Suite | View from room

5. Four Seasons Resort Maui at Wailea

Wailea

You Jin

NT$30,862

NT$38,703 total

includes taxes & fees

Sep 6 - Sep 7

6. Fairmont Kea Lani Maui

Wailea

Brian

NT$34,787

NT$43,513 total

includes taxes & fees

Sep 21 - Sep 22

7. Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

Rashonner

NT$25,291

NT$31,902 total

includes taxes & fees

Sep 26 - Sep 27

8. Ho‘olei Villas at Grand Wailea

Wailea

Justin Robert

NT$54,481

NT$66,729 total

includes taxes & fees

Sep 16 - Sep 17

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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Upcountry Maui.

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr Kihei HI

NT$23,172

NT$29,380 total

Oct 3 - Oct 4

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI

NT$6,713

NT$9,655 total

Sep 27 - Sep 28

includes taxes & fees

8.6/10 Excellent! (1,813 reviews)

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr Lahaina HI

NT$14,408

NT$18,946 total

Sep 5 - Sep 6

includes taxes & fees

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Pool Spa Hot tub Breakfast included Waterpark

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

Venture to top sights like Haleakala National Park as you discover Upcountry Maui—a relaxing area also known for its island views.

See all hotels in Upcountry Maui

Top Upcountry Maui Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent

"Place is very big and has a lot of things to do including a swim-up bar and multiple types of pools. It was a great experience in Maui!"

The Westin Maui Resort & Spa, Ka'anapali

10/10 Excellent

"Gorgeous grounds Unbeatable location close to village and shops and dining Lots of corners to sit and chill, and pools and great view It was very hard to find shade tho as when too windy the staff closes umbrellas Rooms could be bigger for sure but overall very nice (even tho basic toiletries, no slippers and a very old filter coffee machine — the key system also had some glitches and we were shut out of the room 3 times at least… The Luau show was outstanding and amazing food! Overall an amazing stay — I’d def go again. 🙌"

Wailea Beach Resort - Marriott, Maui

10/10 Excellent

"Lovely, partial ocean view room in a quiet location. Housekeeper was excellent, keeping our room in pristine condition. However the room decor was dark and dated for such a quality resort. A stunning location."

The Ritz-Carlton Maui, Kapalua

10/10 Excellent

"Loved this property. Views were amazing."

Four Seasons Resort Maui at Wailea

10/10 Excellent

"Loved every moment we spent there! Best decision to stay at Four Seasons for our honeymoon trip :)"

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 NT$9,655

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.

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Check availability on Upcountry Maui 5 Star Hotels

Our top choices for Upcountry Maui 5-star hotels

1. Grand Wailea Maui, A Waldorf Astoria Resort