A barren volcanic landscape with rugged terrain and distant mountains.

Five Star Hotels in Upcountry Maui

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Check availability on Upcountry Maui 5 Star Hotels

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Upcountry Maui 5-star hotels

A pool with a waterfall feature, surrounded by palm trees and a stone structure.
An aerial view of a beach resort with rows of sun loungers, palm trees, and a view of the ocean.
A resort with multiple buildings, a beach, and a mountainous backdrop.
A spacious balcony with a view of a pool and palm trees, furnished with wicker chairs and a coffee table.

1. Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort
Wailea
United States
nicholas gaetano
S$1,235
includes taxes & fees
28 Oct - 29 Oct
Grand Wailea Maui, A Waldorf Astoria Resort
A resort with a large pool, palm trees, and a view of the ocean.
A gazebo with white columns and a metal roof, surrounded by lush tropical plants and a small water feature.
A woman in a swimsuit standing by a pool with a view of the ocean and palm trees.
A beach with palm trees and a rainbow over the ocean.

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

The Westin Maui Resort & Spa, Ka'anapali
Kannapali Beach Area
United States
Eugene
S$693
includes taxes & fees
11 Nov - 12 Nov
The Westin Maui Resort & Spa, Ka'anapali
A resort pool area with a central fountain, surrounded by lounge chairs and palm trees, leading to the ocean.
A balcony with wicker furniture, a view of the ocean, palm trees, and a mountain in the distance.
A resort with a pool, beach, and mountain view.
A bar area with a curved counter, multiple bar stools, and a view of palm trees and the ocean at dusk.

3. Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
Wailea
United States
Quinn
S$1,641
includes taxes & fees
21 Oct - 22 Oct
Four Seasons Resort Maui at Wailea
A pool area with lounge chairs and palm trees, overlooking the ocean.
An aerial view of a coastal area with a sandy beach, clear turquoise waters, and dense green forest.
A golf course with a pool and resort buildings.
An outdoor dining area with tables and chairs, palm trees, and string lights against a backdrop of the ocean and sky.

4. The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
Kapalua
United States
TAMIKA
S$1,455
includes taxes & fees
16 Oct - 17 Oct
The Ritz-Carlton Maui, Kapalua
A water park with multiple slides and a pool area surrounded by lush greenery and palm trees.
A deck with two lounge chairs facing a scenic ocean view, a wooden floor, and a modern architectural design.
A serene outdoor seating area with two tables covered in white tablecloths and wooden stools, overlooking a coastal view with the ocean and a distant island.
A well-maintained golf course with a clear view of the ocean and a winding path.

5. Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui
Wailea
United States
Christina
S$981
includes taxes & fees
21 Oct - 22 Oct
Wailea Beach Resort - Marriott, Maui
A staircase with a view of a garden, palm trees, and a bridge.
A resort pool area with lounge chairs, umbrellas, and palm trees.
A resort with a large swimming pool, palm trees, and a view of the ocean.
A balcony with a view of the ocean and sunset.

6. Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
Wailea
United States
James
S$1,639
includes taxes & fees
15 Oct - 16 Oct
Fairmont Kea Lani Maui
A poolside area with a fire pit, lounge chairs, and umbrellas.
A bar area with a view of palm trees and the ocean at sunset.
A spacious indoor area with a high ceiling, large windows, and a view of the ocean.
A room with a view of the ocean and lush greenery.

7. Hotel Wailea Maui

Hotel Wailea Maui
Wailea
United States
Rashonner
S$1,374
includes taxes & fees
1 Nov - 2 Nov
Hotel Wailea Maui
A spacious living area with a high ceiling, a dining set, and a sofa facing a large window overlooking the ocean at sunset.
A living room with a sofa, chairs, a coffee table, and a view of the ocean.
A coastal golf course with a view of the ocean, a clear sky, and a golfer on the green.
A resort with multiple buildings, a swimming pool, and a beachfront.

8. The Resort at Kapalua Bay, Maui

The Resort at Kapalua Bay, Maui
Lahaina
United States
John
S$1,920
includes taxes & fees
14 Nov - 15 Nov
The Resort at Kapalua Bay, Maui
A resort with thatched-roof structures, a pool with a waterfall, and wooden railings.
A multi-level hotel atrium with a central bar, outdoor seating, and multiple balconies.
A spacious kitchen with a large island, wooden cabinets, and a view of the ocean.
A pool with a waterfall feature, lounge chairs, and palm trees under a sunset sky.

9. Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
Wailea
United States
Justin Robert
S$2,698
includes taxes & fees
10 Nov - 11 Nov
Ho‘olei Villas at Grand Wailea
A resort with multiple bungalow-style buildings, a swimming pool, and a beach.
A resort with a beach, a swimming pool, and a large building.
A hotel room with a large bed, a desk with a chair, a view of the ocean, and a balcony with a hanging light fixture.
A beachfront property with a large tree, a well-maintained lawn, and a view of the ocean.

10. Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
Lahaina
United States
AURA MARINA
S$540
includes taxes & fees
7 Nov - 8 Nov
Royal Lahaina Bungalows & Spa
A staircase with a view of a garden, palm trees, and a bridge.
A resort with multiple buildings, a swimming pool, and a view of the ocean.
A hotel lobby with a large arched window overlooking a beach, several wooden chairs, and ambient lighting.
A resort with multiple swimming pools, palm trees, and a view of the ocean.

11. Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
Wailea
United States
Sze Wai
S$4,053
includes taxes & fees
24 Oct - 25 Oct
Fairmont Kea Lani Maui Villa Experience
A spacious living room with a large window, a ceiling fan, a sofa, a coffee table, and a TV.
A modern living room with a wooden coffee table, a sofa with blue cushions, a dining area with wicker chairs, and a kitchen with a refrigerator.
A modern kitchen with white cabinets, a marble island, and a view of the ocean.
A modern living room with a wicker chair, a blue sofa, and a dining area in the background.

12. Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
Central Kihei
United States
Mae
Oceanfront Kihei Paradise Vistas
A balcony with a wooden table, a bottle of champagne, and a flower arrangement.
A kitchen with a microwave, a knife block, a bottle of Veuve Clicquot champagne, and two glasses on a marble countertop.
A living room with a blue sofa, a coffee table, and a TV on the wall. There is a balcony with a view of the ocean and palm trees.
A hotel with multiple balconies, a well-maintained lawn, and palm trees.

13. 2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
Central Kihei
United States
Carrie
2 2 Oceanview Modern Resort Vistas
A resort pool area with a hot tub, lounge chairs, and palm trees.
A golf course with a water body, trees, and a distant mountain.
A wooden bridge over a pond, a well-maintained lawn, and a building with a balcony.
A resort with a swimming pool, palm trees, and a mountainous backdrop.

14. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
Wailea
S$2,161
includes taxes & fees
19 Oct - 20 Oct
Villa, Garden View, 2-bedroom
A room with a large glass door leading to a balcony with a view of the ocean and palm trees.
A modern kitchen with a large island, a glass top stove, and a view of the ocean.
A spacious living area with a view of the ocean, a dining area, and a kitchen.
A spacious living area with a large window overlooking the ocean, a ceiling fan, and a wooden floor.

15. Kapalua Bay Villas Resort by KBM

Kapalua Bay Villas Resort by KBM
Kapalua
United States
Mariana
S$1,193
includes taxes & fees
31 Oct - 1 Nov
Kapalua Bay Villas Resort by KBM
A resort with a pool, outdoor seating, and a view of the ocean.
A modern kitchen with a built-in microwave, a dining area with wooden chairs, and a large window offering a view.
A modern living room with a large TV, a dining area, and a kitchen.
A hotel with multiple balconies, a swimming pool area, and palm trees.

16. Aloha Chic Penthouse Vistas

Aloha Chic Penthouse Vistas
Central Kihei
United States
Shirley
Aloha Chic Penthouse Vistas
A rooftop terrace with a view of the ocean, palm trees, and outdoor seating.
A modern living room with a sofa, coffee table, and a decorative lamp.
A living room with a sofa, coffee table, TV, and a ceiling fan.
View from room

17. Hale Ona Loa HOL-102 by KBM

Hale Ona Loa HOL-102 by KBM
Kaanapali
Hale Ona Loa HOL-102 by KBM
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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.
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI
S$404
1 Nov - 2 Nov
includes taxes & fees
8.6/10 Excellent! (1,913 reviews)
Royal Lahaina Resort & Bungalows
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr Lahaina HI
S$748
30 Oct - 31 Oct
includes taxes & fees
Hyatt Regency Maui Resort & Spa
Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa

2605 Kaanapali Pkwy Lahaina HI
S$617
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Sheraton Maui Resort & Spa
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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

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

See all hotels in Upcountry Maui
A barren volcanic landscape with rugged terrain and distant mountains.
Photo by Project Forever

Top Upcountry Maui Hotel Reviews

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

10/10 Excellent
"We were here with our adult children for a family trip and really enjoyed the pools, spa, Spago, the complementary car service and every employee we came in contact with! A great trip!"
Quinn 5-night trip
Posted 11 days ago
Four Seasons Resort Maui at Wailea

Find out more about Upcountry Maui

Stay in Luxury: 5 Star Hotels in Upcountry Maui

There's nothing wrong with enjoying the finer things in life. Indulge your every desire on your upcoming leisure time. Treat yourself with a stay in a 5-star hotel during your Upcountry Maui trip. You'll join the multitudes of holidaymakers who have made Upcountry Maui so fashionable recently. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Upcountry Maui and indulge in the finer things in life for a while.

5-Star Hotels in Upcountry Maui

You'll have a wonderful time at one of these 5-star hotels. Exceptional customer care, luxurious bedding, and deeply relaxing spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A body scrub that will leave you feeling refreshed and alive? Butler services? Whatever it is your heart desires, you're bound to find it here. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs. 

But you aren't going to spend your entire holiday in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Upcountry Maui are waiting for you to relax after an exciting day.

Make Your Escape

The results are in, and Upcountry Maui 5-star hotels are the place to be when you book your next holiday. If you've been dreaming about a holiday set here, then go ahead and book it. It's time to plan your next great escape -- this is a great time to find 5-star hotel deals in Upcountry Maui! Choose one of our Upcountry Maui 5-star hotels today and soothe yourself in luxe surroundings at your convenience.

Expedia India is rated 4 stars by Feefo based on 1038 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 S$404
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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