Search Cottages in Upcountry Maui

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Check prices for these dates

In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Cottages in Upcountry Maui

Adorable 1930's Gingerbread House....Permitted!
Exterior

Adorable 1930's Gingerbread House....Permitted!

9.8 out of 10, Exceptional, (12)
"My wife and I enjoyed our stay. House is perfect for a couple and we enjoyed the animals making their rounds throughout the property each day. Eve was an outstanding hostess and made sure we had everything we needed and enjoyed our stay. If we get to Maui again, we will definitely stay in the Gingerbread House again."
The price is AED 1,010
AED 2,184 total
includes taxes & fees
7 Sep - 8 Sep
Adorable 1930's Gingerbread House....Permitted!
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Exterior

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

9.6 out of 10, Exceptional, (188)
"We had an amazing stay in Hana at the cottage. It’s clean and well equipped. Beautiful view from the kitchen and bedroom. Has a nice private outdoor space. "
The price is AED 810
AED 1,884 total
includes taxes & fees
4 Sep - 5 Sep
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Secluded cottage on Tropical flower farm
Outdoor dining

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (265)
"The cottage was great. Check-in was stress-free and Ms. Rebecca was always responsive. "
The price is AED 1,084
AED 2,039 total
includes taxes & fees
14 Sep - 15 Sep
Secluded cottage on Tropical flower farm
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Outdoor dining

Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops

10.0 out of 10, Exceptional, (71)
"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."
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Cozy Beach Bungalow +Bikes & Pickleball Gear
Exterior

Cozy Beach Bungalow +Bikes & Pickleball Gear

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. "
Cozy Beach Bungalow +Bikes & Pickleball Gear
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

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

10/10 Excellent
"Wonderful stay and views, Staff was very helpful, beach right out the hotel, Great breakfast every morning."
Carl 7-night trip
Posted 3 days ago
Royal Lahaina Resort & Bungalows
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent
"Had a great time. Excellent staff."
Sharon Marie 8-night trip
Posted 6 days ago
OUTRIGGER Kaanapali Beach Resort

Frequently asked questions

How much do cottages in Upcountry Maui cost?
You'll pay between AED 810 and AED 1,084 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 16 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 vacation 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!