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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
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16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for Upcountry Maui cottages

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

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Hana Town Center
9.6 out of 10, Exceptional, (191)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
The price is €512
includes taxes & fees
15 Jan - 16 Jan 2026
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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hana
10.0 out of 10, Exceptional, (90)
"Very unique property near Hana. Great experience!"
United States
Keith R.
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Outdoor dining
Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (281)
"This was a great location, comfortable cute little cottage."
United States
Briana B.
The price is €488
includes taxes & fees
7 Jan - 8 Jan 2026
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

Cozy cottage nestled on our 5 acre Organic fruit farm
Kaʻeleku
10.0 out of 10, Exceptional, (9)
"We loved our stay! The cottage was super cute and the hosts went above and beyond by welcoming us! My favorite place we stayed and a perfect overnight for Hāna."
United States
Allison W.
The price is €447
includes taxes & fees
13 Jan - 14 Jan 2026
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

Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Central Kihei
10.0 out of 10, Exceptional, (73)
"Fantastic property that was a perfect escape and great location for exploring Maui. Would definitely stay again. "
United States
Matt B.
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Exterior
Maui bungalow - Walk to Kaanapali beach

Maui bungalow - Walk to Kaanapali beach

Maui bungalow - Walk to Kaanapali beach
Lahaina
9.2 out of 10, Wonderful, (10)
"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."
United States
Kristin M.
Maui bungalow - Walk to Kaanapali beach
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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Top Upcountry Maui Hotel Reviews

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent
"Was an amazing resort "
Peyman 6-night trip
Posted 12 hours ago
OUTRIGGER Kaanapali Beach Resort

Find out more about Upcountry Maui

Upcountry Maui Cottages information

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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?
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