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

9.8 out of 10, Exceptional, (150)
"Loved our time here. Good location to everything on the island. "
Evergreen Cottage @ Maui Adventure Villa

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

9.6 out of 10, Exceptional, (167)
"We thoroughly enjoyed the privacy of this location while being centrally located in Hāna. The privacy shading on the deck allowed us to enjoy the wonderful view and sounds of the ocean. The cottage is cute and well furnished. The outdoor shower was great after a day of hiking and swimming. "
The price is AED 973
AED 1,880 total
includes taxes & fees
1 Dec - 2 Dec
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (238)
"great property- felt like the rain forest! quiet clean and location was perfect to explore Hana. would definitely stay again."
The price is AED 1,084
AED 2,050 total
includes taxes & fees
3 Dec - 4 Dec
Secluded cottage on Tropical flower farm

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 1,139
AED 2,003 total
includes taxes & fees
28 Nov - 29 Nov
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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

10.0 out of 10, Exceptional, (179)
"The guest house is a wonderful traditional design, and its private location is surrounded with tropical landscaping and a view of the hills and ocean. Casual yet luxurious comfortable furnishings, and well supplied for beach trips. Hank is a great host. Aloha. "
ALOHA NOV. DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub

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

9.8 out of 10, Exceptional, (214)
"We’ve stayed in three other vacation rentals in Hanne and this is our favorite. Quiet, great location and comfortable. We’ll definitely stay here the next time we visit Hana."
The price is AED 1,080
AED 2,021 total
includes taxes & fees
20 Dec - 21 Dec
Great location between Hana Town and Hamoa Beach, private, family-friendly

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

10.0 out of 10, Exceptional, (190)
"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!

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

10.0 out of 10, Exceptional, (135)
"Love staying at this beautiful cottage and being so close to the beach and great restaurants and shopping. Truly the best way to experience this side of the island of Maui. Elaine is a wonderful host and very helpful. The pool is my favorite experience here can't wait to return."
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

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

10.0 out of 10, Exceptional, (139)
"We had a wonderful time in this private little cottage. Good location, with shops and restaurants nearby. Great ocean views. Btw, the Maui Aquarium is a great stop for an afternoon and lunch in the outdoor restaurant was very good. "
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!

Now with optional car add-on

10.0 out of 10, Exceptional, (138)
"The convenience, the communication with the owners, The little extra touches, and the ease of access and accommodations were superb. We would definitely stay there again."
Now with optional car add-on

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

10.0 out of 10, Exceptional, (173)
"Ohana is a very important belief in Hawaii. At Villa Paola, they go even further and embrace you into their Famiglia. First of all, words cannot describe the beauty of this home. The moment you enter the driveway, the lush greenery envelopes you and you literally feel like you have found paradise. You enter the home to find everything you want and more. The house is incredibly clean and welcoming. The bed is so comfortable, and the bathroom exquisite. You could lose yourself in the gallery...
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004

Cozy Maui 'Treehouse' with lovely views and amenities

10.0 out of 10, Exceptional, (90)
"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!

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

9.4 out of 10, Exceptional, (30)
"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

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

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! "
The price is AED 1,286
AED 2,188 total
includes taxes & fees
24 Dec - 25 Dec
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

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 918
AED 3,096 total
includes taxes & fees
28 Nov - 29 Nov
Beach Bungalow with Cruiser Bikes & Pickleball!

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

9.0 out of 10, Wonderful, (29)
"Well cared for home and close to everything in old town!! We enjoyed a comfortable stay at this cozy home!"
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!

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

Luxury Upcountry retreat with breathtaking views!

10.0 out of 10, Exceptional, (74)
"Stayed here a few years ago, and we loved our return stay. Very peaceful in a beautiful setting with incredible views, this is a unique and fantastic way to experience Maui. Great, clear and concise communications with David. We look forward to returning…mahalo!"
Luxury Upcountry retreat with breathtaking views!
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

3.5 star property
8.6 out of 10, Excellent, (3350)
"Several people we visited were “owners” at AKS and were very friendly; one even said “thank you for staying at Shores; I hope you make the choice to stay here again.” The view out our balcony of the pool area and the ocean from afar was beautiful. "
The price is AED 1,300
AED 1,642 total
includes taxes & fees
8 Dec - 9 Dec
Aston Kaanapali Shores

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2627)
"Some things were not working in our room, e.g. master bedroom balcony door would not open, table in the balcony was very wobbly, dryer was not operating properly. All these issues were resolved by the staff when I called them, but they seem to be basic checks that property management should have checked before giving us keys and not have me call about them. "
The price is AED 808
AED 2,899 total
includes taxes & fees
10 Dec - 11 Dec
OUTRIGGER Honua Kai Resort & Spa

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1080)
"Great property in perfect location adjacent to walking path & snorkeling beach. We loved our one-bedroom unit and enjoyed the resorts amenities including pools and restaurants. Well maintained, very clean, friendly staff, wish we could have extended our stay, but not easy to do at a timeshare property like you can at a hotel. That said, we wouldn't hesitate to return, next time for a longer visit. Mahalo!"
The price is AED 1,759
AED 2,075 total
includes taxes & fees
2 Dec - 3 Dec
The Westin Ka'anapali Ocean Resort Villas
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 918 and AED 1,286 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.