A barren volcanic landscape with rugged terrain and distant mountains.

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Upcountry Maui cottages

Exterior

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

Adorable 1930's Gingerbread House....Permitted!
Makawao
9.8 out of 10, Exceptional, (13 reviews)
"a beautiful property and a nice cottage! We completely enjoyed our time here."
United States
Kathy W.
The price is AU$783
includes taxes & fees
4 Sept - 5 Sept
Adorable 1930's Gingerbread House....Permitted!
House (3 Bedrooms) | Front of property

2. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
The price is AU$1,555
includes taxes & fees
31 Aug - 1 Sept
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
Interior

3. Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Hana
10.0 out of 10, Exceptional, (524 reviews)
"Absolutely wonderful place in paradise. Hosts were amazing. Brough us fresh eggs and fruit. Amazing view and love the kitty too!"
United States
Diann
The price is AU$549
includes taxes & fees
16 Aug - 17 Aug
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Outdoor dining

4. 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, (77 reviews)
"Fantastic property that was a perfect escape and great location for exploring Maui. Would definitely stay again. "
United States
Matt B.
The price is AU$758
includes taxes & fees
25 Aug - 26 Aug
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Exterior

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (101 reviews)
"Beautiful grounds, great location close to secluded beach."
United States
Mark S.
The price is AU$778
includes taxes & fees
16 Aug - 17 Aug
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Terrace/patio

6. Beach Bungalow w/ Cruiser Bikes & Pickleball!

Beach Bungalow w/ Cruiser Bikes & Pickleball!
Lahaina
9.6 out of 10, Exceptional, (21 reviews)
"Kitchen was stocked with everything we needed a cook a few meals during our stay. "
United States
laurie s.
The price is AU$1,316
includes taxes & fees
22 Aug - 23 Aug
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.
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Top Upcountry Maui Hotel Reviews

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent
"Staff was amazing. We absolutely loved our stay there"
Roxane 4-night trip
Posted 1 hour 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?
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.

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