Upcountry Maui 5 Stars Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Upcountry Maui 5 Star Hotels

This weekend
Next weekend

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

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.0 out of 10, Wonderful, (1003)
"A great place to relax."
The price is NT$26,758
NT$33,495 total
includes taxes & fees
Aug 10 - Aug 11
The Ritz-Carlton Maui, Kapalua

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1000)
"Fantastic staff! "
The price is NT$21,039
NT$24,818 total
includes taxes & fees
Sep 5 - Sep 6
Four Seasons Resort Maui at Wailea

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
8.8 out of 10, Excellent, (1001)
"This place was AMAZING!!!"
The price is NT$20,449
NT$26,053 total
includes taxes & fees
Aug 17 - Aug 18
Grand Wailea Maui, A Waldorf Astoria Resort

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1000)
"Beautiful resort "
The price is NT$24,768
NT$30,972 total
includes taxes & fees
Aug 29 - Aug 30
Fairmont Kea Lani Maui

Hotel Wailea, Relais & Chateaux - Adults Only

5.0 star property
9.4 out of 10, Exceptional, (1001)
"This place is truly amazing! The service is impeccable, the resort is beautiful, and the views are breathtaking. I can’t wait to return again."
The price is NT$25,421
NT$31,743 total
includes taxes & fees
Aug 13 - Aug 14
Hotel Wailea, Relais & Chateaux - Adults Only

Montage Kapalua Bay

5.0 star property
9.8 out of 10, Exceptional, (201)
"Super nice "
The price is NT$29,764
NT$38,270 total
includes taxes & fees
Aug 29 - Aug 30
Montage Kapalua Bay

Ho‘olei Villas at Grand Wailea

5.0 star property
9.6 out of 10, Exceptional, (42)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
The price is NT$62,640
NT$75,828 total
includes taxes & fees
Aug 22 - Aug 23
Ho‘olei Villas at Grand Wailea

2 2 Oceanview Modern Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (3)
"This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!"
2 2 Oceanview Modern Resort Vistas

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."
The price is NT$57,049
NT$69,049 total
includes taxes & fees
Aug 30 - Aug 31
Fairmont Kea Lani Maui Villa Experience

Wailea Luxury Hilltop Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (2)
"very nice place and location 🤗"
Wailea Luxury Hilltop Resort Vistas

Centrally Located Elegant Vistas

5.0 star property
10.0 out of 10, Exceptional, (1)
"Love this Kihei home! Centrally located! It is very clean. We love that they have beach chairs and towels on hand. Overall great experience stay!"
Centrally Located Elegant Vistas

Oceanfront Kihei Paradise Vistas

5.0 star property
10.0 out of 10, Exceptional, (2)
"This property was clean, quiet, and had excellent security. The barbecue grill was easy to use. They had sandless beach towels, which worked so well. The view was beautiful! I want to go again next year. "
Oceanfront Kihei Paradise Vistas
Save an average of 15% on thousands of hotels when you're signed in

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.
Still don't see what you're looking for?
See all properties in Upcountry Maui.
You can also use these popular filters to refine your search.
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 Haleakalā Visitor Center and Haleakala Crater as you discover Upcountry Maui—a relaxing area also known for its island views.

Maui Island featuring landscape views

Top Upcountry Maui Hotel Reviews

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$7,082

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.