Search Cottages in Upcountry Maui

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
14 Nov - 16 Nov
In two weeks
21 Nov - 23 Nov
In one month
5 Dec - 7 Dec
In two months
2 Jan - 4 Jan

Featured Cottages in Upcountry Maui and around

Terrace/patio
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
10.0 out of 10, Exceptional, (86)
"Enjoyed the property. More rustic than I am used to. "
United States
Thomas S.
The price is €593
includes taxes & fees
3 Dec - 4 Dec
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
Exterior
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
9.6 out of 10, Exceptional, (189)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Exterior
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
10.0 out of 10, Exceptional, (89)
"The place was beautiful and the gardens are absolutely breathtaking!!! It was so peaceful and perfect for my husband and I after a VERY long day making the drive to Hana and hiking the Pipiwai Trail to see the Waimoku Falls!!! Only wish we could have stayed here longer on our trip!"
United States
Dena V.
The price is €483
includes taxes & fees
24 Nov - 25 Nov
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Outdoor dining
Secluded cottage on Tropical flower farm
Secluded cottage on Tropical flower farm
9.4 out of 10, Exceptional, (274)
"The cottage was great. Check-in was stress-free and Ms. Rebecca was always responsive. "
United States
La Tecia P.
The price is €497
includes taxes & fees
11 Nov - 12 Nov
Secluded cottage on Tropical flower farm
Exterior
Cozy cottage nestled on our 5 acre Organic fruit farm
Cozy cottage nestled on our 5 acre Organic fruit farm
10.0 out of 10, Exceptional, (8)
"This property is absolutely gorgeous and the place had everything we could want for our one night stay. The fresh fruit was such a lovely touch. Wish we had stayed longer!"
United States
Kate S.
Cozy cottage nestled on our 5 acre Organic fruit farm
Outdoor dining
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
10.0 out of 10, Exceptional, (72)
"We absolutely loved our stay at this amazing cottage! A lot of really good eating locations within walking distance as well as the beach! We enjoyed using the beach equipment provided and the rental was so well equipped with everything you need! So happy we found this little gem!"
United States
Erika G.
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Exterior
Beach Bungalow w/ Cruiser Bikes & Pickleball!
Beach Bungalow w/ Cruiser Bikes & Pickleball!
9.2 out of 10, Wonderful, (10)
"From the beginning Dan had GREAT communication! Not only was Dan responsive, he provided a plethora of information of places to eat and visit! Our stay was wonderful. We are a family of seven and there was a place for everyone to go inside the bungalow. The lanai is GREAT, a wonderful place to have coffee and enjoy the still of the morning or hang out with family and have food and drinks in the evenings! A home away from home! Their place even provided a few body boards and other items for beach...
United States
Tyesha M.
The price is €797
includes taxes & fees
18 Nov - 19 Nov
Beach Bungalow w/ 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upcountry Maui Hotel Reviews

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent
"The property is beautiful and quiet. "
Jeffery 2-night trip
Posted 3 days ago
OUTRIGGER Kaanapali Beach Resort

Find out more about Upcountry Maui

Upcountry Maui Cottages information

Number of reviews
Accommodation
 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Upcountry Maui cost?
You'll pay between and per night for cottages in Upcountry Maui. No matter your budget, a terrific stay is only a click or two away on Expedia. 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?
Upcountry Maui has cottages on offer. Click on your travel dates, enter your destination and start planning your perfect trip today.
Why book your cottage in Upcountry Maui with Expedia?
Booking a cottage in Upcountry Maui is as simple as deciding on your travel dates and choosing an ideal place for a holiday in nature. From chic retreats to affordable stays and cottages that include perks like a pool, Expedia has something for all tastes and styles. As for the best offers around? We've got you covered!
How can I find cheap cottages in Upcountry Maui?
A wonderful way to track down cheap cottages in Upcountry Maui is with Expedia's user-friendly filter tool. Refine your search results by star rating, amenities and budget to access unbeatable rates in a couple of clicks.

Explore a world of travel with Expedia