Search Cottages in Upcountry Maui

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 23 Cottages in Upcountry Maui with updated reviews, rates, and availability.

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

9.0 out of 10, Wonderful, (32)
"I was traveling for work and the house was convenient for my meetings and very spacious to work in and rest in. I found my stay lovely. "
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!

Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

10.0 out of 10, Exceptional, (78)
"Lovely single room home set in elevated tropical surroundings with terrific long view to ocean. We highly recommend the location and property tour by owner"
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

Evergreen Cottage @ Maui Adventure Villa

9.8 out of 10, Exceptional, (156)
"Beautiful property "
Evergreen Cottage @ Maui Adventure Villa

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (247)
"We enjoyed our stay in this special part of Hana. Quiet setting and peaceful surroundings. Great for a family getaway. "
The price is SAR 1,256
SAR 2,263 total
includes taxes & fees
7 Mar - 8 Mar
Secluded cottage on Tropical flower farm

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

9.6 out of 10, Exceptional, (177)
"The place was very clean and close to whatever you planned on doing. Communication was great. "
The price is SAR 994
SAR 1,892 total
includes taxes & fees
20 Feb - 21 Feb
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

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

10.0 out of 10, Exceptional, (142)
"This unit works out perfect for my husband and I is incredibly comfortable and pleasant. Working with the manager is very easy and she is very accommodating. I’ve already booked for next year!"
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!

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

10.0 out of 10, Exceptional, (67)
"I don't know what to say other than wow! This was the rare place where the pictures don't quite do it justice. It's set inside of what feels like tropical rainforest and just so peaceful and serene. We ended up spending more time at the place than we anticipated just because it was so relaxing. The outdoor shower, the screened-in porch, the bathtub! This place was so tastefully appointed and lovingly set up that it's worth a trip to Hana just to get to stay here. "
The price is SAR 1,219
SAR 2,092 total
includes taxes & fees
8 Mar - 9 Mar
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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

10.0 out of 10, Exceptional, (178)
"We enjoyed the large outdoor space and private pool. The owners are very responsive and provide drinking water on tap. Lots of great artwork throughout the space. The outdoor bar area is especially nice. The pool is not heated and is very deep so can be a little brisk. Recommend mapping the address on your phone rather than looking at the location in the listing on the VRBO site as the map there is not accurate.. "
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004

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

10.0 out of 10, Exceptional, (193)
"The cottage was very nice, beautifully kept and comfortable. We arrived late at night and the lights were left on to welcome us to our home away from home. Each room had nice clean ceiling fans and opening windows which made for a breezy comfortable stay. The view was spectacular and the sunsets incredible. We felt very comfortable and relaxed during our stay. The location is just minutes away from the beach and a nice Beach Walk to many options for dining out and shopping. Although with the...
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!

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

9.8 out of 10, Exceptional, (221)
"The grounds were lovely. The house was clean. We stayed one night on our way to the national Park. Had a lovely time barbecueing.."
Great location between Hana Town and Hamoa Beach, private, family-friendly

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

9.8 out of 10, Exceptional, (18)
"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!

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

10.0 out of 10, Exceptional, (138)
"Miss Elaine’s place was fantastic! We had everything we needed. The place was clean, not too far from the beach, and it was close to stores and restaurants. We rented a car and only had to fuel up 2 times during the 2 weeks we were there. The pool was amazing, our daughter (5 years old) had so much fun hanging out at the pool. It was nice on days when we did not want to do too much. Beach days were awesome because she had 2 coolers, 3 beach chairs, 2 boogie boards and plenty of towels available...
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

MARCH CANCELLATION SPECIAL 349/NT 7nt min. Private, Romantic Cottage

10.0 out of 10, Exceptional, (183)
"We had a wonderful stay at this peaceful and beautiful house. The entire process was smooth, and the house is well furnished. We’ve come to really enjoy the Haiku area It’s rural enough for quiet but within 15 minutes to Kahului and several small towns, and quite handy for day trips to Hana or Haleakalā. If you want an escape from the tourist areas of Maui, this is a wonderful option. "
MARCH CANCELLATION SPECIAL 349/NT 7nt min. Private, Romantic Cottage

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 SAR 1,500
SAR 3,887 total
includes taxes & fees
19 Mar - 20 Mar
Beach Bungalow with Cruiser Bikes & Pickleball!

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

9.2 out of 10, Wonderful, (23)
"Our family of 6 really enjoyed staying here. There was enough space for everyone and it really is just a 5 minute walk to Airport Beach (also known as Kahekili). We had no problems with cleaniless. The little complex the cottage is apart of is quiet and well maintained. Our family spent a lot of time on the lanai enjoying the ocean view and breezes. We would definietly stay here again. "
Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd

Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01

9.8 out of 10, Exceptional, (184)
"The property was exactly as described. Beautiful large fruit tree garden property within walking distance to Waianapanapa State Park's black sand beach. Home was very clean and well-stocked. The owner's housekeeper left fresh fruit for us on the day we checked in. Owner was very responsive to questions before our arrival."
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01

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

Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach

9.6 out of 10, Exceptional, (55)
"This unit is very well equipped with everything you need. The space is comfortable and spacious for two. Has a nice private patio area. It is easy to get to from the airport by car, has grocery options within a few miles, and is within walking distance of the beach and several restaurants. The owner is very responsive to needs. We'd be happy to stay her again if in Maui."
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach

Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!

9.8 out of 10, Exceptional, (11)
"This was a great place to stay. We loved coming home to it. The owners were very nice. The little grey cat was so welcoming and we appreciated his company. Our only "complaint" would be the beds. They are a tad uncomfortable. But we all survived unscathed. Thanks Jon and Jody"
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!

Cozy Maui 'Treehouse' with lovely views and amenities

10.0 out of 10, Exceptional, (91)
"Peaceful property in a locals neighborhood. Wake up to birdsong. Close to all amenities, including the beach, by foot and by car, which was very nice. Enjoyed our stay. Mahalo!"
Cozy Maui 'Treehouse' with lovely views and amenities
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.
Don't see what you're looking for?
See all available properties in Upcountry Maui
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Upcountry Maui

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3456)
"The resort had easy access to various beaches and the amenities were great! "
The price is SAR 1,268
SAR 1,606 total
includes taxes & fees
17 Mar - 18 Mar
Aston Kaanapali Shores

Aston Maui Kaanapali Villas

3.0 star property
8.6 out of 10, Excellent, (2344)
"Great place and wonderful staff! A few small negatives… Only thing I didn’t like was all of the extra fees at the end. I think it was $35/day added plus a lot of little taxes. Parking is difficult as well, but we’re young and didn’t affect us much with a little walking to get to the room. Just a heads up for any elderly visitors. "
Aston Maui Kaanapali Villas

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2698)
"Everything was excellent."
The price is SAR 1,704
SAR 3,731 total
includes taxes & fees
12 Mar - 13 Mar
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 SAR 994 and SAR 1,500 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 23 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.