Find 5 Star Hotels in Upcountry Maui, HI from ￥61,190

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Upcountry Maui 5 Star Hotels

Tonight
Mar 23 - Mar 24
Tomorrow
Mar 24 - Mar 25
This weekend
Mar 27 - Mar 29
Next weekend
Apr 3 - Apr 5

Our top choices for Upcountry Maui 5-star hotels

Property grounds

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,002 reviews)
"10/10 service, amazing room with gorgeous view! "
United States
Timothy
The price is ￥150,472
￥189,025 total
includes taxes & fees
Apr 11 - Apr 12
Four Seasons Resort Maui at Wailea
Exterior detail

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,000 reviews)
"Great location. Clean hotel, friendly staff. Beautiful surroundings. "
Canada
Jamie
The price is ￥170,400
￥211,737 total
includes taxes & fees
Apr 17 - Apr 18
Fairmont Kea Lani Maui
3 outdoor pools, cabanas (surcharge), sun loungers

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
5.0 star property
Kapalua
9.2 out of 10, Wonderful, (1,000 reviews)
"It’s Nice Hotel , our room was overlooking the pool, nice and quiet area. Staff were extremely nice and accommodating. "
United States
Ronen
The price is ￥143,148
￥181,085 total
includes taxes & fees
Mar 24 - Mar 25
The Ritz-Carlton Maui, Kapalua
Bar (on property)

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,001 reviews)
"Everything was exceptional! Great property, quiet and peaceful "
United States
Abdulla
The price is ￥157,480
￥196,398 total
includes taxes & fees
Apr 19 - Apr 20
Hotel Wailea, Relais & Chateaux - Adults Only
On the beach, beach towels, snorkeling, surfing

The Resort at Kapalua Bay, Maui

The Resort at Kapalua Bay, Maui
5.0 star property
Lahaina
9.6 out of 10, Exceptional, (209 reviews)
"The views are next level. We enjoyed the pools, spa, restaurant and more. It was our second stay there and definitely going back. "
United States
Mandy D
The price is ￥413,839
￥491,277 total
includes taxes & fees
Apr 15 - Apr 16
The Resort at Kapalua Bay, Maui
Restaurant

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (45 reviews)
"Womderful home, terrific service, access to hotel amenities was key."
United States
ALAN
The price is ￥333,759
￥406,542 total
includes taxes & fees
Apr 17 - Apr 18
Ho‘olei Villas at Grand Wailea
Aerial view

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
9.2 out of 10, Wonderful, (7 reviews)
"Clean room and staff is super friendly. Would stay here again "
United States
Rene
The price is ￥54,600
￥73,269 total
includes taxes & fees
Apr 13 - Apr 14
Royal Lahaina Bungalows & Spa
Balcony

2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
5.0 star property
Central Kihei
9.8 out of 10, Exceptional, (7 reviews)
"The condo was very clean, loved all of the decor, was very beautiful. Had everything you could possibly need in kitchen and bathrooms. Would definitely stay again! Everyone we talked to was very nice and helpful! "
United States
Paulina
2 2 Oceanview Modern Resort Vistas
Luxury Apartment | Beach/ocean view

Wailea Luxury Hilltop Resort Vistas

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

Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
5.0 star property
Wailea
9.8 out of 10, Exceptional, (6 reviews)
"It’s a decent hotel to stay for the family."
United States
Sze Wai
Fairmont Kea Lani Maui Villa Experience
Luxury Condo | Living area | 90-inch Smart TV with digital channels, Hulu, streaming services

Centrally Located Elegant Vistas

Centrally Located Elegant Vistas
5.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"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!"
United States
Edwin
Centrally Located Elegant Vistas
Condo (2 Bedrooms) | View from room

NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach Ks-616

NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach Ks-616
5.0 star property
Kaanapali
NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach Ks-616
Condo (2 Bedrooms) | Terrace/patio

Kapalua Ridge Villas KBM Resorts 2 Units, 2 Bedrooms KRV Ml-3535

Kapalua Ridge Villas KBM Resorts 2 Units, 2 Bedrooms KRV Ml-3535
5.0 star property
Kapalua
Kapalua Ridge Villas KBM Resorts 2 Units, 2 Bedrooms KRV Ml-3535
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 ￥87,099 per night from Apr 12 to Apr 13
￥87,099
￥112,599 total
Apr 12 - Apr 13
includes taxes & fees
9.2/10 Wonderful! (1,012 reviews)
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.
PoolSpaHot tubBreakfast includedWaterpark
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
View over Haleakala crater, at 3000 ft. Make sure that the skies are clear before heading to Haleakala, otherwise this view could be totally blocked by clouds. #AboveItAll
Photo by Project Forever
Open Photo by Project Forever

Top Upcountry Maui Hotel Reviews

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

10/10 Excellent
"Four Seasons is worth every penny, every time. They are excellent. This property and the service is unmatched in the area. I stayed all of last week and then came back. Staff is so excellent. Property is gorgeous. It's just perfect. A lot of things aren't worth the price these days, but I have to say this hotel is worth the money. 5 stars."
Chelsea 1-night trip
Posted 4 days ago
Four Seasons Resort Maui at Wailea

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 ￥61,190

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.

Explore a world of travel with Expedia