Upcountry Maui Adventure Sport Hotels, Hawaii: Upcountry Maui Hotel Guide

A barren volcanic landscape with rugged terrain and distant mountains.

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 Adventure Sport Hotels

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Upcountry Maui adventure hotels

A spacious living room with a large glass coffee table, a sofa, and a fireplace.

1. Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.

Makawao

David

includes taxes & fees

17 Nov - 18 Nov

A rustic wooden house with a large window and a door, surrounded by lush greenery and palm trees.

2. Adorable 1930's Gingerbread House....Permitted!

Makawao

Kathy W.

includes taxes & fees

16 Nov - 17 Nov

A bamboo structure with a sloped roof, surrounded by rocks and plants.

3. Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Makawao

Lisa B.

includes taxes & fees

17 Nov - 18 Nov

A spacious kitchen with a large island, wooden flooring, and modern lighting fixtures.

4. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

Haiku

Amy C.

includes taxes & fees

30 Nov - 1 Dec

A modern house with a covered porch, a dining area, and a barbecue grill.

5. Paia Inn

Paia

Austin

includes taxes & fees

14 Dec - 15 Dec

A paved pathway leading to a gate with red pillars, surrounded by lush greenery and palm trees, with a view of the ocean in the background.

6. Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Hana

Sonja W.

includes taxes & fees

4 Dec - 5 Dec

A spacious balcony with wicker furniture, a view of the ocean, and a mountain in the distance.

7. Hilton Grand Vacations Club Maui Bay Villas

North Kihei

Chloe

includes taxes & fees

10 Dec - 11 Dec

A water park with multiple slides and a pool area surrounded by lush greenery and palm trees.

8. Wailea Beach Resort - Marriott, Maui

Wailea

Joseph

includes taxes & fees

10 Dec - 11 Dec

A beach with clear blue water, rocky shore, and palm trees.

9. Condo w/ Lanai at Beginning of Road to Hana!

Paia

Zachary S.

includes taxes & fees

15 Nov - 16 Nov

A balcony with a table set for two, featuring a bottle of wine and two glasses.

10. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

North Kihei

pablo

includes taxes & fees

3 Dec - 4 Dec

View all properties

Top Upcountry Maui Hotel Reviews

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent

"We enjoyed our stay at the Outrigger Kaanapali Beach Resort. Friendly staff, clean amenities. Restaurants are expensive in this area but there's also ABC, Whole Foods and Safeway supermarkets nearby where you can get some essentials."

Aston Mahana at Kaanapali

10/10 Excellent

"Our apartment was more than we could have asked for! Full size kitchen and living room was amazing. Everything was clean and ready for us to use. Our bedroom was perfect with a comfortable bed and a screen door to open and listen to the ocean! The bathroom had 2 sinks which was perfect for us. We will definitely be back!"

Frequently asked questions

How much do hotels for couples in Upcountry Maui cost?

Prices for hotels for couples in Upcountry Maui range between €300 and €2,832 per night. No matter your budget, you're sure to find the perfect place that'll make both your sweetheart and your wallet smile! These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your hotel for couples in Upcountry Maui with Expedia?

We think that a holiday with your sweetheart should be a piece of cake, so if you're seeking a hotel for couples in Upcountry Maui at a great price, Expedia can help. Keep costs down and choose a comfortable motel, or splurge and book an opulent hotel escape to treat the one you love the most.

How can I find cheap hotels for couples in Upcountry Maui?

Expedia can help you look for cheap hotels for couples in Upcountry Maui. Make use of our filter tool to select amenities, budget and star rating to refine your search and reserve a terrific place to get away with your love in just a few clicks.

Explore a world of travel with Expedia

Maui Holiday Rentals

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Upcountry Maui Adventure Sport Hotels

Our top choices for Upcountry Maui adventure hotels

1. Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.

2. Adorable 1930's Gingerbread House....Permitted!

3. Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16