Search Cottages in Upcountry Maui

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

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, (133)
"There was an ungodly amount of rules at this property. So much so that we left the last two nights and booked a resort instead. There were a good amount on the listing, but I just figured the owners must have been taken advantage of in the past, so they are super firm upfront. The first thing they ask you to do, which most places also ask, is that you read the rule book. But holy moly, the rules are out of control. One example: "NO MARCO POLO. ITS ANNOYING." No slime, no play doh, no loud noises...
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Evergreen Cottage @ Maui Adventure Villa
Kitchen, Dining Area leading to Screened Lanai
Evergreen Cottage @ Maui Adventure Villa
9.8 out of 10, Exceptional, (146)
"During my time in Maui it was a work trip and Johns property was the perfect spot to relax and recharge after a long days of work and adventure. The location was far enough to where there was no noise from the city but close enough to where it wasnt a burden to get to the beaches and stores. Will definitely stay again and recommend."
Evergreen Cottage @ Maui Adventure Villa
ALOHA DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
Welcome to your Private Romantic Cottage in Paradise while enjoying Maui!
ALOHA DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
10.0 out of 10, Exceptional, (174)
"We loved the place. All details have been thought of. We felt at home. Love outside shower and garden. Hardly recommend this place. Great Hawaiian hospitality. MERCI BEAUCOUP"
ALOHA DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
Secluded cottage on Tropical flower farm
Outdoor dining
Secluded cottage on Tropical flower farm
9.6 out of 10, Exceptional, (233)
"This house was perfect for our 2 night stay in Hana. I loved how private and secluded the house was yet still 5 minutes from Hana. Everything was perfect, 10/10 would highly recommend."
Secluded cottage on Tropical flower farm
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, (171)
"It was a nice relaxing and private place to stay"
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
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, (212)
"nothing fancy, but clean, private and a great location."
The price is SAR 1,013
SAR 1,726 total
includes taxes & fees
24 Sep - 25 Sep
Great location between Hana Town and Hamoa Beach, private, family-friendly
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, (165)
"This home was the perfect place to stay in Hana. It was in great location and clean. The air conditioning in the bedroom worked great to cool down the entire space. It had great amenities and was quiet. Also had a great view of the ocean."
The price is SAR 994
SAR 1,920 total
includes taxes & fees
29 Sep - 30 Sep
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
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, (228)
"This property and plantation is exquisite. From booking to arrival, all communication was clear and Precise. A Warm arrival with the feeling of home, it was truly utopia here in Hana. Mahalo."
The price is SAR 1,313
SAR 2,236 total
includes taxes & fees
28 Sep - 29 Sep
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
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, (16)
"Pros: The home was spacious, conveniently located and accurate to the listing photos. We appreciated that the host provided shampoo, conditioner and body wash in the bathroom. The two chilled bottles of water in the fridge were also a nice touch. Cons: There was a surprising amount of noise from the road (cars speeding, blasting music and a few fireworks). The bathroom and bedroom doors were also tricky to close. The floors were dirty when we arrived."
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
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, (27)
"This was the perfect fit for me and my son! I got the bedroom and he got the pull out couch. It was a wonderful experience and the added bonus of keyless entry was one less thing I had to keep track of!"
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
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"
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Luxury Upcountry retreat with breathtaking views!
Luxury Upcountry retreat with breathtaking views!
10.0 out of 10, Exceptional, (72)
"Wonderful Property as described. David was the consummate host."
Luxury Upcountry retreat with breathtaking views!
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, (89)
"We had a fantastic stay at Pam’s Treehouse. She made us feel like at home from when we arrived. Pam is passionate about the island and we were amazed by her story. We were amazing by how well stuffed her place is from the water filter to the aftersun and antifog for the snorkel masks. We hope to come back in the future!"
Cozy Maui 'Treehouse' with lovely views and amenities
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, (98)
"Clean, safe, well stocked, basic accommodations. Short walk to Paia Center —shops, restaurants grocery, etc. Friendly, helpful owner"
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
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, (136)
"Great setup! Very good location for seeing all of Maui. Very well equipped. Owner very helpful. Unobstructed view of sunrise over the Pacific."
Now with optional car add-on
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, (136)
"This was perfect for everything my wife and I wanted for our honeymoon stay in beautiful Maui. The owners have many accommodations on the property that we felt went above and beyond expectation. The short walk to the beach was perfect for sunset viewing, hanging with the turtles, and more! Shops, restaurants, etc., are all within walking distance from the property and super convenient. Can’t recommend this place enough! "
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
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, (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
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
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, (7)
"We loved our stay! Perfect location! Fully equipped and spacious home. We will come back! "
The price is SAR 1,313
SAR 3,684 total
includes taxes & fees
28 Sep - 29 Sep
Beach Bungalow with Cruiser Bikes & Pickleball!
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, (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!
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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.
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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, (3254)
"Nice property in a great location. Very clean and maintained property. Very nice pool. Rooms are spacious. It’s older but very nice. "
The price is SAR 1,143
SAR 1,458 total
includes taxes & fees
21 Oct - 22 Oct
Aston Kaanapali Shores
Aston Maui Kaanapali Villas
Exterior
Aston Maui Kaanapali Villas
3.0 star property
8.6 out of 10, Excellent, (2264)
"This resort is the best kept secret on Kaanapali Beach! Studio suites had full stainless kitchen, ice cold air conditioning, and is right on the beach with easy access. Plenty of chairs at the pool and the grounds are spotless. This an an older Hawaii resort with only two story buildings and free parking right outside the rooms. There are hotel style rooms in one building but they don't provide the full kitchen. Go for a studio! This is the third time staying here and never had a problem. Used...
The price is SAR 1,122
SAR 1,611 total
includes taxes & fees
26 Sep - 27 Sep
Aston Maui Kaanapali Villas
OUTRIGGER Honua Kai Resort & Spa
Exterior
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2607)
"Overall I thought the property was great! Easy walk to the beach and other hotel restaurants. We enjoyed several meals at Dukes restaurant on site. There are some areas where the property needs updates such as the pool/hot tub tiles, showers, and chairs on balcony. "
The price is SAR 1,264
SAR 3,478 total
includes taxes & fees
2 Oct - 3 Oct
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 SAR877 and SAR877 per night. These stays offer a chance to reconnect with nature — at a price you can afford. 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 22 cottages on offer. Enter your destination and travel dates and organize your next escape today.
Why book your cottage in Upcountry Maui with Expedia?
Expedia has some wonderful cottages in Upcountry Maui, so start planning for an unforgettable stay on nature’s doorstep. If you have a fixed budget, select how much you’re willing to spend and the star rating of your property. Or, use our filters to search for cottages with a kitchen or a pool. We’ll help you find the perfect pad whatever your plans or bank balance.
How can I find cheap cottages in Upcountry Maui?
With Expedia’s filter tool, sourcing cheap cottages in Upcountry Maui couldn’t be simpler. To find accommodations that’ll make your bank balance smile, fine-tune your search results by budget, amenities and star rating.