Search Cottages in Upcountry Maui

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Compare 22 Cottages in Upcountry Maui with updated reviews, rates, and availability.

Evergreen Cottage @ Maui Adventure Villa
Kitchen, Dining Area leading to Screened Lanai

Evergreen Cottage @ Maui Adventure Villa

9.8 out of 10, Exceptional, (154)
"Great location, great environment, great neighborhood. Nice, quiet and peaceful place to stay after a day of adventures! "
Evergreen Cottage @ Maui Adventure Villa
Secluded cottage on Tropical flower farm
Outdoor dining

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (240)
"Had a wonderful time staying in this lovely cottage set in the midst of all the Hawaiian trees and flowers. Was just a visual delight. The house was clean and wonderful. Thank You"
The price is AED 1,230
AED 2,232 total
includes taxes & fees
19 Jan - 20 January 2025
Secluded cottage on Tropical flower farm
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Cozy Hana Bay View Cottage with covered lanai, new vinyl decking and siding.

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

9.6 out of 10, Exceptional, (172)
"Enjoyed our stay at this spot in Hana. The owners do a great job at providing essentials and even had beach chairs which came in so handy! Loved the stay and a perfect way for us to rest after doing the Highway to Hana. The only thing: the GPS didn’t quite bring us here but we figured it out!"
The price is AED 1,084
AED 2,025 total
includes taxes & fees
10 Jan - 11 January 2025
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hamoa Bay Bungalow

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

10.0 out of 10, Exceptional, (64)
"We had an amazing time in Hana! The cabin"
The price is AED 1,194
AED 2,076 total
includes taxes & fees
7 Jan - 8 January 2025
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
ALOHA NOV. DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
Welcome to your Private Romantic Cottage in Paradise while enjoying Maui!

ALOHA NOV. DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub

10.0 out of 10, Exceptional, (181)
"We both felt so comfortable and at home in this lovely open concept accommodation. The owner and manager were very helpful. They both offered hand picked oranges, tangerines, bananas and lemons that grew on the property. The bed was very comfortable and the kitchen was well appointed with everything one could need. We will definitely be back. "
ALOHA NOV. DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
Beautiful coastal decor in this charming cottage.

Plantation Style cottage short walk to beach and town Permit STPH2013/0004

9.8 out of 10, Exceptional, (99)
"Perfect place to stay when planning on windsurfing Hookipa. "
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Cottage and pool area with surrounding tropical foliage

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

10.0 out of 10, Exceptional, (136)
"The property is absolutely incredible. Elaine provided all the information in advance and instructions were all very clear. The place itself is nicely setup. The kitchen had all the things needed for some quick meals and probably more if you wanted to do some additional cooking. For us at least, the proximity to amazing local food kept us largely out of the kitchen. The rooms were nicely setup, and the owners even had a pack'n'play for our toddler which was great. The pool was of course the...
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Evenings at the bar and patio

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

10.0 out of 10, Exceptional, (174)
"Absolutely had a great experience staying there."
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
Best views on the Island from every room!

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

10.0 out of 10, Exceptional, (141)
"Cozy, clean, absolutely priceless view, easy access to ocean and poised for sunset watching indoors and out. Amenities were perfect and everything we needed was a short drive away (other beaches, amazing food, shopping, local life, food trucks, and community. "
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Room

1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!

9.0 out of 10, Wonderful, (30)
"The host were very generous with information and helping us. We had a terrific stay"
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
Living area

Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!

10.0 out of 10, Exceptional, (191)
"We had a fabulous time and snorkeled every day at one of the best beaches on the island! Terry responded quickly when we didn't have hot water and had the hot water tank replaced as soon as possible. The cottage is very spacious and equipped with many extras in the kitchen. The bathrooms could use some more towels and wash rags, but we were able to wash the existing towels throughout the week because there's a washer/dryer and laundry detergent. There's no AC which bothered some in our party,...
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
Now with optional car add-on
Drone view from ocean -- arrow points to cottage roof.

Now with optional car add-on

10.0 out of 10, Exceptional, (139)
"Stayed for a week for our honeymoon. Very private. Everything you could want has been provided including warm coats and hats, snorkeling gear, boogie boards, etc. Very gracious hosts who also rented us their car"
Now with optional car add-on
Private, Serene & Cute Cottage. Ocean Views & A/C. Near Hana Hwy.
Palm Cottage - a cute cottage in a serene setting with coastal ocean views.

Private, Serene & Cute Cottage. Ocean Views & A/C. Near Hana Hwy.

10.0 out of 10, Exceptional, (84)
"Everthing was as advertised. Robert answered all our questions. The property was secluded. Eveything we needed for our visits to the local community were available. "
Private, Serene & Cute Cottage. Ocean Views & A/C. Near Hana Hwy.
Great location between Hana Town and Hamoa Beach, private, family-friendly
View from screened-in patio

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

9.8 out of 10, Exceptional, (217)
"We loved this little spot. Fabulous view that we enjoyed with the moon reflecting off the ocean, a huge lawn to play on and super close to Koki, Hamoa and Hana. We would have loved to stay longer! "
The price is AED 992
AED 1,886 total
includes taxes & fees
25 Jan - 26 January 2025
Great location between Hana Town and Hamoa Beach, private, family-friendly
Cozy Maui 'Treehouse' with lovely views and amenities
Spectacular sunsets viewed from your lanai/patio deck

Cozy Maui 'Treehouse' with lovely views and amenities

10.0 out of 10, Exceptional, (91)
"Enjoyed staying in a quiet peaceful neighborhood within walking distant to the beach. Having our own space and deck was relaxing after a busy day exploring the island."
Cozy Maui 'Treehouse' with lovely views and amenities
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
Living area

Cute Plantation Cottage; Walk into Wailuku Town; Central Location!

9.8 out of 10, Exceptional, (17)
"This place was a great option for staying on Maui and being able to get to just about everywhere. It’s a great place to begin a trip down the Road to Hana, and there are a lot of good places to eat in the city. Highly suggest trying JJ’s Tacos food truck just blocks away. The bed was comfortable and the AC worked very well for a good nights sleep. "
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining

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

9.4 out of 10, Exceptional, (31)
"Very comfortable and a great location. We enjoyed our stay."
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd
Perfect for enjoying the sunset, grilling dinner, and dining al fresco.

Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd

9.0 out of 10, Wonderful, (22)
"We had a very enjoyable stay at this rental, and it had everything we needed. Great location and well-maintained. It's a little bit outdated, yes, but that didn't bother me at all considering it looked exactly like the listing (even better in my opinion), and was very clean, functional, and still very charming. We really enjoyed eating dinner and watching sunsets on the adorable lanai, and the shared pool in the complex was great! We would definitely rent this place again if we ever return to...
Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Plantation Style Cottage

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

10.0 out of 10, Exceptional, (230)
"It was perfect! We loved Hāna, the bungalow, the people, the location. Truly magical! The property managers were fantastic, helped with navigating the area. It’s so perfect you don’t want it to get spoiled. Hana is special, and the bungalow was perfect! "
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Beach Bungalow with Cruiser Bikes & Pickleball!
Vaulted ceilings and endless windows create an open space with tropical views!

Beach Bungalow with Cruiser Bikes & Pickleball!

9.0 out of 10, Wonderful, (8)
"The property is very clean and we loved having the lanai available with the bbq. Definitely comes in handy with a big family who doesnt want to go out every night. We'd absolutely stay here again."
The price is AED 2,204
AED 4,727 total
includes taxes & fees
13 Jan - 14 January 2025
Beach Bungalow with 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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Other property types in Upcountry Maui

Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3392)
"We were a party of 12, with ages varying from 2-60. We shared two suites, which they helped us be right next to each other. The property was a little older and showing its age but rooms were spacious. The suites were well appointed, with well stocked kitchens for cooking and lots of storage space. Free activities were great and kept us busy, including their Christmas party, stocking votes, ukulele lessons and lei making ($). Pools were great for all ages. Being right on the beach was perfect,...
The price is AED 1,466
AED 1,837 total
includes taxes & fees
6 Jan - 7 January 2025
Aston Kaanapali Shores
Royal Kahana Maui by OUTRIGGER
Pool

Royal Kahana Maui by OUTRIGGER

3.0 star property
8.0 out of 10, Very Good, (1323)
"The room was well designed with a great view of the ocean. It had cooking facility and excellent for a linger stay. The rooms have mirrors which helps with light view and makes the room bigger. The rooms also had a washer dryer and together made our stay comfortable and enjoyable"
Royal Kahana Maui by OUTRIGGER
OUTRIGGER Honua Kai Resort & Spa
Exterior

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2651)
"This place was absolutely amazing! Very clean, friendly staff, spacious and quiet but lively at the same time, amazing balconies with unbelievable views and an overall perfect place to get away! The outdoor areas were clean and inviting- 3 pools and 5 hot tubs. We all loved the food trucks that were within walking distance. Parking was close and easy. Would recommend this place to everyone! It had a condo but resort feel which was super nice! "
The price is AED 1,669
AED 3,654 total
includes taxes & fees
10 Jan - 11 January 2025
OUTRIGGER Honua Kai Resort & Spa
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.

Frequently asked questions

How much do cottages in Upcountry Maui cost?
Cottages in Upcountry Maui range between AED 992 and AED 2,204 per night. These retreats offer a chance to touch base with nature — at a price you can afford. 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?
Take your pick of 22 cottages in Upcountry Maui. Whether you’re traveling with the family, as a duo or with a group of friends, Expedia makes it simple to find the ideal space.
Why book your cottage in Upcountry Maui with Expedia?
Expedia has some superb cottages in Upcountry Maui, so start packing your bags for an unforgettable vacation on nature’s doorstep. If you need to stick to a budget, choose how much you want to spend and your preferred property star rating. Or, try out our filters to search for cottages with a hot tub or a kitchen. We’ll help you find the right digs whatever your plans or bank balance.
How can I find cheap cottages in Upcountry Maui?
Expedia is here to help you track down cheap cottages in Upcountry Maui. To discover a superb stay in a couple of clicks, try out our handy filter tool to refine your search by budget, amenities and star rating.