Upcountry Maui 5 Stars Hotels

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Check availability on Upcountry Maui 5 Star Hotels

Tonight
Jun 28 - Jun 29
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Jun 29 - Jun 30
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Jul 4 - Jul 6
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Jul 11 - Jul 13

Top Upcountry Maui 5 Stars Hotels

Four Seasons Resort Maui at Wailea
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1001)
"One of the best resorts in Hawaii "
The price is P42,135
P49,703 total
includes taxes & fees
Jul 14 - Jul 15
Four Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort
2 bars/lounges, 2 poolside bars, swim-up bar

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
9.0 out of 10, Wonderful, (1002)
"We had the best time! The property is absolutely gorgeous and the weather was perfect. "
The price is P54,238
P67,091 total
includes taxes & fees
Jul 14 - Jul 15
Grand Wailea Maui, A Waldorf Astoria Resort
The Ritz-Carlton Maui, Kapalua
3 outdoor pools, cabanas (surcharge), sun loungers

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.0 out of 10, Wonderful, (1001)
"Excellent hotel and staff. "
The price is P53,390
P66,649 total
includes taxes & fees
Jun 29 - Jun 30
The Ritz-Carlton Maui, Kapalua
Fairmont Kea Lani Maui
View from room

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1001)
"Great place for family."
The price is P45,622
P57,152 total
includes taxes & fees
Jul 21 - Jul 22
Fairmont Kea Lani Maui
Hotel Wailea, Relais & Chateaux - Adults Only
Outdoor spa tub

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 P44,787
P56,167 total
includes taxes & fees
Jul 6 - Jul 7
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
On the beach, beach towels, snorkeling, surfing

Montage Kapalua Bay

5.0 star property
9.8 out of 10, Exceptional, (201)
"Super nice "
The price is P62,269
P80,065 total
includes taxes & fees
Jul 19 - Jul 20
Montage Kapalua Bay
Ho‘olei Villas at Grand Wailea
Outdoor pool, sun loungers

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 P162,265
P195,081 total
includes taxes & fees
Jul 19 - Jul 20
Ho‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui Villa Experience
View from property

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 P192,246
P230,097 total
includes taxes & fees
Jul 22 - Jul 23
Fairmont Kea Lani Maui Villa Experience
Wailea Luxury Hilltop Resort Vistas
Private kitchen

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
2 2 Oceanview Modern Resort Vistas
Outdoor pool, pool umbrellas, sun loungers

2 2 Oceanview Modern Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (2)
"This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!"
2 2 Oceanview Modern Resort Vistas
Oceanfront Kihei Paradise Vistas
Outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas, sun loungers

Oceanfront Kihei Paradise Vistas

5.0 star property
10.0 out of 10, Exceptional, (1)
Oceanfront Kihei Paradise Vistas
Centrally Located Elegant Vistas
Balcony

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
Upscale Luxurious Ocean Resort Vistas
BBQ/picnic area

Upscale Luxurious Ocean Resort Vistas

5.0 star property
Upscale Luxurious Ocean Resort Vistas
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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.
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy, Lahaina, HI
The price is P32,827 per night from Jul 15 to Jul 16
P32,827
P41,995 total
Jul 15 - Jul 16
includes taxes & fees
9/10 Wonderful! (835 reviews)
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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 Haleakalā Visitor Center and Haleakala Crater as you discover Upcountry Maui—a relaxing area also known for its island views.

See all hotels in Upcountry Maui
Maui Island showing 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 P14,252

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.