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Browse Select Upcountry Maui Cottages

On the beach
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
10.0 out of 10, Exceptional, (130)
"It was incredible. The view and uniqueness of this cottage and property are superb. My husband and I had never in our lives been to the islands until this stay. (10 day stay). We knew we wanted a quiet, non-resort property and this was perfect! Everything you could need or want is just a few minutes away by car. We even walked to a near-by restaurant which was wonderful! Sitting on the deck watching and hearing the gentle ocean waves and many birds was surreal. It was truly a vacation to...
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
SUMMER DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
10.0 out of 10, Exceptional, (167)
"This is our second time at what we call Hank's Place (or Hank's Hawaiian Hideaway, sometimes). It is tied with one other place (in Spain) as our favorite share rental in the world. Hank is a wonderful and reliable host -- there when you need him; not there when you don't. Best of all, it is a FRAGRANCE-FREE RENTAL!!! (Not counting the soaps and shampoos that are provided; but the bedding is, the most important part; and also, no annoying potpourri.). Although you are on the "rainy side" of the...
SUMMER DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
Pool | Outdoor pool, a heated pool
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
10.0 out of 10, Exceptional, (129)
"We had a nice stay. Nice and private place in a nice quiet neighborhood. The cabin came stocked with all the amenities one would need."
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
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Exterior
Cozy Maui 'Treehouse' with lovely views and amenities
10.0 out of 10, Exceptional, (87)
"The Treehouse suited my wife and me perfectly. I think it would be a challenge to fine a place that is more peaceful and tranquil, as far as a vacation rental in Kihei. It is also a nice place to view the sunsets."
Cozy Maui 'Treehouse' with lovely views and amenities
Fridge, microwave, oven, stovetop
Beach Bungalow with 1967 International Scout!
10.0 out of 10, Exceptional, (4)
"Everything was great and we had a marvelous time! The accommodations were perfect and met our needs very well. I would love to come back again sometime!"
The price is £641
includes taxes & fees
22 May - 23 May
Beach Bungalow with 1967 International Scout!
On the beach, sun-loungers, beach towels
Now with optional car add-on
10.0 out of 10, Exceptional, (135)
"It is an amazing property. It’s combines views amenities privacy and above all the hosts are the most accommodating helpful, knowledgeable and out great human beings."
Now with optional car add-on
Property grounds
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
10.0 out of 10, Exceptional, (169)
"Our stay was amazing! Our hosts went above and beyond! Looking forward to coming back!!"
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Pool
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
10.0 out of 10, Exceptional, (224)
"We had a great time staying in Hana and would love to stay here again."
The price is £478
includes taxes & fees
19 May - 20 May
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Exterior
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
10.0 out of 10, Exceptional, (189)
"This beautiful property is perfect for those that want to get away from the large resorts and have nice place to come home to after a day of swimming, snorkeling, or sightseeing. It has one of the best stocked kitchens to do your own cooking along with a ton extras for your beach adventures. We stayed 7 days with our 6 and 8 years girls and they never once said they were bored. They entertained themselves in the pool that is right out the back door and chased endless butterflies that little...
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
Fridge, microwave, oven, stovetop
Steps from the Ka'anapali Royal Golf Course
10.0 out of 10, Exceptional, (4)
"Beautiful, relaxing, nice people"
Steps from the Ka'anapali Royal Golf Course
Outdoor pool
Luxury Upcountry retreat with breathtaking views!
10.0 out of 10, Exceptional, (71)
"The Jungalow was an amazing spot to begin our Hawaiian vacation. It was the perfect spot to explore upcountry and East Maui. We loved being only an hour drive to sunrise and a good spot to begin Road to Hana as well. So much adventure to explore around here. We enjoyed dinner at Mama’s one night (what a treat), but loved coming back to the Jungalo to rest our tired legs the other nights. A good soak in the hot tub is the perfect end to day whether watching the sunset or the stars twinkle. Loved...
Luxury Upcountry retreat with breathtaking views!
Sun-loungers, beach towels
Indulge, just steps to pristine beaches, restaurants & shopping.
10.0 out of 10, Exceptional, (18)
"Very well appointed and located, near restaurants and within a short drive (10-15 mins) of great beaches. Highly recommend."
Indulge, just steps to pristine beaches, restaurants & shopping.
Property grounds
Evergreen Cottage @ Maui Adventure Villa.
9.8 out of 10, Exceptional, (143)
"Was very helpful and great with communication. Hopefully we will get to stay at John’s property again! Gorgeous location and perfect of you are planning on stay near paia."
Evergreen Cottage @ Maui Adventure Villa.
Sun-loungers, beach towels
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
9.8 out of 10, Exceptional, (92)
"My wife and I enjoyed our stay at this Vrbo very much. The check in/check out was easy. The detached unit felt private and roomy. It was very clean. The place was as advertised. No surprises. Easy walk to Paia with its restaurants and shopping. Close to beaches and to airport. Good overall location on Maui."
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
Fridge, microwave, oven, stovetop
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
9.8 out of 10, Exceptional, (14)
"My husband and I stayed here a few nights on our trip to Maui, and this was the perfect spot! It was a great location, close to the airport, central location on the island to go and do lots of fun activities, and overall a very pleasant stay! Thank you!"
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
Beach nearby, sun-loungers, beach towels
Great location between Hana Town and Hamoa Beach, private, family-friendly
9.8 out of 10, Exceptional, (208)
"Nice small house just outside Hana, but close to everything. 1min to food trucks and stores, 5min to two beaches (and Huli Huli Chicken). It is a good place to start for day trips to do all the road to Hana things without hurry and be the first at Waimoku Falls, Waiʻānapanapa State Park or Lava Tube. If we (family of 4) come back to Hana, we happily would stay here again."
The price is £418
includes taxes & fees
21 May - 22 May
Great location between Hana Town and Hamoa Beach, private, family-friendly
Outdoor dining
Secluded cottage on Tropical flower farm
9.6 out of 10, Exceptional, (225)
"You will feel right at home in this very clean, cozy lush environment. If you’re looking for a change of pace tucked in a beautiful environment look no further. My 15-year-old son and I stayed here for 4 nights and felt right at home. We enjoyed cooking in the kitchen, and although they could have a few more cooking items, we were able to make all of our favorite meals from home. I would highly recommend this place for any family and friends seeking a longer stay than most in Hana."
The price is £453
includes taxes & fees
24 May - 25 May
Secluded cottage on Tropical flower farm
Beach
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
9.6 out of 10, Exceptional, (160)
"Very nice no complaints would book again"
The price is £412
includes taxes & fees
21 May - 22 May
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
TV
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
9.4 out of 10, Exceptional, (29)
"Very comfortable and a great location. We enjoyed our stay."
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
Sun-loungers, beach towels
Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd
9.4 out of 10, Exceptional, (20)
"Based up previous review, we expected it to be simple, but clean and fully functioning. Surfaces were not all clean, some small things didn't work, and it was very difficult to communicate with the hosts (gave us no local contact email or cell # and VRBO app didn't work for contacting host). It would have been great to have some sort of cottage notebook with info about local areas, beaches, restaurants, and driving distances from house. No local info provided; had to search everything ourselves....
Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd
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See all available properties in Upcountry Maui
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.

Other property types in Upcountry Maui

Outdoor pool
Aston Mahana at Kaanapali
3.5 star property
9.0 out of 10, Wonderful, (1469)
"Very nice and very well taking care of "
The price is £593
includes taxes & fees
4 Jun - 5 Jun
Aston Mahana at Kaanapali
4 outdoor pools
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2531)
"I loved everything about this resort. "
OUTRIGGER Honua Kai Resort & Spa
Hypo-allergenic bedding, in-room safe, blackout curtains
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (2998)
"Amazing views and right on the beach and pools were never packed "
The price is £268
includes taxes & fees
3 Jun - 4 Jun
Aston Kaanapali Shores
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.

Upcountry Maui Cottages information

Number of reviews
1,803
Accommodation
22 Cottages
Lowest Price
£412
Highest Price
£641

Frequently asked questions

How much do holiday cottages in Upcountry Maui cost?
Prices for holiday cottages in Upcountry Maui range between £412 and £641 per night. No matter your budget, you’re sure to find an ideal place to get in tune with nature. 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 holiday cottages are there in Upcountry Maui?
Choose from 22 holiday cottages in Upcountry Maui. Whether you’re travelling with the entire family, as a table-for-two or with a group of old friends, Expedia makes it simple to find your ideal place.
Why book your cottage in Upcountry Maui with Expedia?
Reserving a cottage in Upcountry Maui is as easy as clicking on your travel dates and selecting an ideal place for a getaway in the outdoors. From upmarket retreats to low-cost stays and holiday cottages that have amenities like a kitchenette, Expedia has something for all traveller tastes. As for the best deals around? We have them too!
How can I find cheap cottages in Upcountry Maui?
Expedia is here to help you easily source cheap cottages in Upcountry Maui. To find a superb stay in a few clicks, simply use our convenient filter tool to tailor your search results by star rating, amenities and budget.

Upcountry Maui Hotel Reviews
Expedia verified reviews

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

5/5 Excellent
"I usually visit Oahu twice a year and decided to give Maui a try. I thought nothing could top Oahu but I was wrong. I absolutely loved everything about my trip and I think a huge reason was this hotel. The staff were incredibly friendly and even remembered my name. Helene at front desk was especially great. Room was clean and newly renovated. The beach was so beautiful, gardens and hammocks offered were so nicely kept, also great restaurant and store on site. You definitely get your moneys worth booking this resort. What I also really loved about this resort was the free cultural activities offered. I was able to make my own lei and it was such a great experience. Overall this hotel is so amazing and I cant wait to visit again."
A verified traveller stayed at OUTRIGGER Kaanapali Beach Resort
Posted 1 day ago
OUTRIGGER Kaanapali Beach Resort