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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Upcountry Maui cottages

A small, rustic cabin with a stone exterior and a wooden door, surrounded by dense foliage.

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

Adorable 1930's Gingerbread House....Permitted!
Makawao
9.8 out of 10, Exceptional, (13 reviews)
"a beautiful property and a nice cottage! We completely enjoyed our time here."
United States
Kathy W.
The price is AU$807
includes taxes & fees
16 Nov - 17 Nov
Adorable 1930's Gingerbread House....Permitted!
A covered outdoor area with a wooden deck, a round table with chairs, and a view of a field with red foliage.

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

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
The price is AU$1,813
includes taxes & fees
30 Nov - 1 Dec
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
A view from a balcony with a wooden railing, overlooking a lush garden and the ocean.

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

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Hana
10.0 out of 10, Exceptional, (538 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
The price is AU$563
includes taxes & fees
11 Nov - 12 Nov
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
A wooden deck with a table and chairs, surrounded by lush greenery.

4. Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (315 reviews)
"The cottage was beautiful just as described. Quiet and relaxing. The host was great and even checked on us because we checked in during a storm. Check in process was so easy. I would definitely recommend."
United States
nancy
The price is AU$803
includes taxes & fees
10 Nov - 11 Nov
Secluded cottage on Tropical flower farm
A house surrounded by dense tropical vegetation.

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (109 reviews)
"Beautiful grounds, great location close to secluded beach."
United States
Mark S.
The price is AU$778
includes taxes & fees
14 Nov - 15 Nov
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
A covered outdoor seating area with a wooden bench, cushioned chairs, and a zebra-patterned rug.

6. Beach Bungalow w/ Cruiser Bikes & Pickleball!

Beach Bungalow w/ Cruiser Bikes & Pickleball!
Kannapali Beach Area
9.6 out of 10, Exceptional, (25 reviews)
"A perfect location with the beach just a short walk away. Lots of space (even for our group of 8!). Hosts were helpful and responsive throughout our process. Highly recommend for your time in Maui."
United States
Jenn P.
The price is AU$1,301
includes taxes & fees
17 Nov - 18 Nov
Beach Bungalow w/ Cruiser Bikes & Pickleball!
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.
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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
Open Photo by Project Forever

Top reviews in Upcountry Maui

A house with a green roof, surrounded by lush tropical plants and trees.
Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center
Makawao

10/10 Excellent

Relaxing place to stay. Plenty of activities. Only thing you need is a car if you want to explore the island.
Australia
Stephen
Reviewed March 1, 2023
Lumeria Maui Educational Retreat Center

Frequently Asked Questions

How much do cottages in Upcountry Maui cost?

Expect to pay between AU$563 and AU$1,813 per night for cottages in Upcountry Maui. No matter your budget, an epic stay is a click away on Expedia. This price was 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 cottages to choose from. Enter your destination and dates and lock in your dream getaway today.

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