Search Upcountry Maui Cottage Accommodations

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
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured Cottages in Upcountry Maui

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. "
The price is AU$646
includes taxes & fees
23 Oct - 24 Oct
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Exterior
Great location between Hana Town and Hamoa Beach, private, family-friendly
Great location between Hana Town and Hamoa Beach, private, family-friendly
9.8 out of 10, Exceptional, (232)
"Good location & great experience"
The price is AU$788
includes taxes & fees
16 Oct - 17 Oct
Great location between Hana Town and Hamoa Beach, private, family-friendly
Exterior
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
10.0 out of 10, Exceptional, (87)
"After eight trips to Hawaii, this is the first place where I really felt I was in paradise. "
The price is AU$841
includes taxes & fees
26 Oct - 27 Oct
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, (272)
"The cottage was great. Check-in was stress-free and Ms. Rebecca was always responsive. "
The price is AU$860
includes taxes & fees
23 Oct - 24 Oct
Secluded cottage on Tropical flower 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)
"This charming cottage is a marvel of great design, surrounded by a beautiful garden. We enjoyed walking through the friendly neighborhood on our way to town. The owners are skilled, organized inn keepers. All contributed to a wonderful week on Maui."
The price is AU$941
includes taxes & fees
14 Nov - 15 Nov
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Exterior
Bungalow walk to beach + Pickleball gear and Bikes
Bungalow walk to beach + Pickleball gear and Bikes
9.2 out of 10, Wonderful, (10)
"We often had the pool to ourselves, occasionally sharing it with at most one other family. The location is convenient and it was easy to get to many different beaches. One thing to be aware of: the loft ceiling is quite low and the space there is tight. The extra twin rollout bed is at the floor level. "
The price is AU$1,440
includes taxes & fees
2 Nov - 3 Nov
Bungalow walk to beach + Pickleball gear and Bikes
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

Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa

10/10 Excellent
"This property was breathtaking! Gorgeous landscaping, felt like paradise. The beach was right there and a walk away. I wish I was on a bit of a higher floor for a better ocean view but it was still wonderful!"
Deneil 3-night trip
Posted 3 hours ago
Sheraton Maui Resort & Spa

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?
Expect to pay between and per night for cottages in Upcountry Maui. No matter your budget, an epic stay is a click away on Expedia. 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 cottages to choose from. Enter your destination and dates and lock in your dream getaway today.

Explore a world of travel with Expedia