Search Cottages in Upcountry Maui

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Upcountry Maui

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004
Pool

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

10.0 out of 10, Exceptional, (193)
"Could not have been better. Cottage is a little jewel. Carrie, the host,is an amazing, kind and helpful person, Highly recommend staying at the cottage."
Hawaiian Cottage and Personal Paradise /BBKM 2013/0004
Secluded cottage on Tropical flower farm
Outdoor dining

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (262)
"Such a beautiful local! Thank you for hosting us. We truly fell in love with Hana and hope to be back."
The price is AED 1,084
AED 2,039 total
includes taxes & fees
18 Jul - 19 Jul
Secluded cottage on Tropical flower farm
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Sun loungers, beach towels

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

10.0 out of 10, Exceptional, (77)
"After eight trips to Hawaii, this is the first place where I really felt I was in paradise. "
The price is AED 1,139
AED 1,992 total
includes taxes & fees
23 Jul - 24 Jul
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Pool

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

10.0 out of 10, Exceptional, (241)
"Very nice accommodations in Hana, Maui. Perfect location and great kitchen! Very prompt response to a new lighting switch request in bathroom. Would stay here again."
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Outdoor pool, a heated pool

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

10.0 out of 10, Exceptional, (146)
"We had a wonderful stay at Elaine's cottage. The location and property were perfect for us. Thanks for a fantastic week. "
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
On the beach

Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!

10.0 out of 10, Exceptional, (151)
"Just the right amount of everything. Comfortable tasteful decor with the benefit of the beach just steps away. Beautiful location and easy access to hiking, snorkeling and outdoor exploration. Enjoyed every second of our week there. "
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Outdoor dining

Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004

10.0 out of 10, Exceptional, (183)
"Great location-convenient to beaches, restaurants but also very private! Villa set in beautifully landscaped yard. Lovely pool for daytime use and when lit up at night."
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
Outdoor dining

Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining

9.2 out of 10, Wonderful, (34)
"Second year we have stayed here. Very quiet on dead end street in Maui Meadows. Beautiful view. Really no issues at all. Will stay here again next year when we return to Maui!"
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
Luxury Upcountry retreat with breathtaking views!
Outdoor pool

Luxury Upcountry retreat with breathtaking views!

10.0 out of 10, Exceptional, (85)
"This was the perfect upcountry spot, with the most beautiful views of Maui - from the balcony, from the hot tub, from the bed! 10/10 will definitely stay here again"
Luxury Upcountry retreat with breathtaking views!
Evergreen Cottage @ Maui Adventure Villa
Property grounds

Evergreen Cottage @ Maui Adventure Villa

9.8 out of 10, Exceptional, (166)
"Beautiful property "
Evergreen Cottage @ Maui Adventure Villa
Great location between Hana Town and Hamoa Beach, private, family-friendly
Beach nearby, sun loungers, beach towels

Great location between Hana Town and Hamoa Beach, private, family-friendly

9.8 out of 10, Exceptional, (230)
"Clean property at a convenient location and reasonable priced. There are many food options nearby and key Hana locations are easily accessible."
Great location between Hana Town and Hamoa Beach, private, family-friendly
Loft Bungalow with Lanai + Bikes & Pickleball gear
Fridge, microwave, oven, stovetop

Loft Bungalow with Lanai + Bikes & Pickleball gear

9.2 out of 10, Wonderful, (10)
"We often had the pool to ourselves, occasionally sharing it with at most one other family. The location is convenient and it was easy to get to many different beaches. One thing to be aware of: the loft ceiling is quite low and the space there is tight. The extra twin rollout bed is at the floor level. "
The price is AED 1,010
AED 3,204 total
includes taxes & fees
20 Jul - 21 Jul
Loft Bungalow with Lanai + Bikes & Pickleball gear
Hawaiian Dream Temple
Outdoor pool

Hawaiian Dream Temple

4.0 star property
Hawaiian Dream Temple
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Beach

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

9.6 out of 10, Exceptional, (187)
"This was a great location and great cottage. Loved our 4 nights here. "
The price is AED 823
AED 1,915 total
includes taxes & fees
20 Jul - 21 Jul
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach
Sun loungers, beach towels

Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach

9.6 out of 10, Exceptional, (60)
"Great little cottage Simple and convenient for my needs Would definitely stay here again!"
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach
HAWAIIAN DREAM TEMPLE - w/Private Hot Tub and Shared Pool - Permit#BBPH2012-0004
Outdoor pool

HAWAIIAN DREAM TEMPLE - w/Private Hot Tub and Shared Pool - Permit#BBPH2012-0004

9.8 out of 10, Exceptional, (84)
"The most beautiful and peaceful tropical getaway! We will be coming back for sure!"
HAWAIIAN DREAM TEMPLE - w/Private Hot Tub and Shared Pool - Permit#BBPH2012-0004
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

How much do cottages in Upcountry Maui cost?
You'll pay between AED 823 and AED 1,139 per night for cottages in Upcountry Maui. No matter your budget, a terrific stay is only a click or two away on Expedia. 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.
How many cottages are there in Upcountry Maui?
Upcountry Maui has 27 cottages on offer. Click on your travel dates, enter your destination and start planning your perfect trip today.
Why book your cottage in Upcountry Maui with Expedia?
Booking a cottage in Upcountry Maui is as simple as deciding on your travel dates and choosing an ideal place for a vacation in nature. From chic retreats to affordable stays and cottages that include perks like a pool, Expedia has something for all tastes and styles. As for the best offers around? We've got you covered!