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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Compare Cottages in Upcountry Maui with updated reviews, rates, and availability.

Lumeria Maui Educational Retreat Center
Exterior

Lumeria Maui Educational Retreat Center

3.5 star property
8.6 out of 10, Excellent, (191)
"After a horrific night at the airport because of the weather and having to find a place the last minute, we were very pleased with Lumeria very accommodating very clean very quiet thank you"
The price is AED 1,220
AED 1,742 total
includes taxes & fees
9 Feb - 10 Feb
Lumeria Maui Educational Retreat Center
Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.
Interior

Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.

10.0 out of 10, Exceptional, (5)
"A lovely, comfortable property. Easy to get to Haleakala National Park from here to hike the volcano."
The price is AED 661
AED 1,363 total
includes taxes & fees
1 Mar - 2 Mar
Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.
Bamboo Valley Inn
Property grounds

Bamboo Valley Inn

3.5 star property
9.4 out of 10, Exceptional, (55)
"Property was very clean and quiet. Owners were great."
Bamboo Valley Inn
Haleakala Sunrise Home, Kula, Maui, Hawaii
Sunset from front deck June 2021

Haleakala Sunrise Home, Kula, Maui, Hawaii

9.8 out of 10, Exceptional, (75)
"Peaceful, quiet retreat in cool upcountry. Beautiful pasture on one side, ocean views on the main side deck. Super comfortable bed, cool mountain breezes. Comfortable couch, and overall stay. Friendly and wonderful hosts, sparkling clean and stylish furnishings. "
The price is AED 1,010
AED 1,797 total
includes taxes & fees
14 Feb - 15 Feb
Haleakala Sunrise Home, Kula, Maui, Hawaii
Bed and Breakfast on the Slopes of Haleakala
Jewel of Keokea Guest-Suite and Orchid Patio

Bed and Breakfast on the Slopes of Haleakala

10.0 out of 10, Exceptional, (51)
"So much to see and do up here. Winery, high quality coffee shops and restaurants are all within 15 mins. Not to mention a huge time savings driving to Haleakala and Hana. Many farms to tour from tequila to chocolate to honey and friendly people everywhere. Speaking of which, our host Lori left us wanting for nothing with laundry service and the best pantry we’ve seen hands down. The sunset walks down Thompson Road were our favourite with the island on full display below you. Much Aloha in...
Bed and Breakfast on the Slopes of Haleakala
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!
maui-hawaii_0079

Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!

10.0 out of 10, Exceptional, (22)
"Natural beauty abounds!"
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!
Clear Bubble Tent w/Queen Size Bed, includes indoor bedroom and bathroom
Property grounds

Clear Bubble Tent w/Queen Size Bed, includes indoor bedroom and bathroom

10.0 out of 10, Exceptional, (17)
"Everything was great and I would give a five star except. For my age, , staying in the bubble overnight impossible without necessary bathroom facilities. Getting up two to three times a night not possible realistically.nbathroom "
The price is AED 1,194
AED 2,064 total
includes taxes & fees
14 Feb - 15 Feb
Clear Bubble Tent w/Queen Size Bed, includes indoor bedroom and bathroom
Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.
Room

Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.

Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.
Spacious Hawaiian Cottage Suite in the Upcountry of Maui!
maui-hawaii_0071201

Spacious Hawaiian Cottage Suite in the Upcountry of Maui!

10.0 out of 10, Exceptional, (9)
"I cannot say enough great things about this little gem. If you’re looking for a special place to celebrate anything - off the beaten path - but easy access to most of the best of Maui, look no further. Shannon and Josh have made this place truly magical. I cannot wait to return! "
Spacious Hawaiian Cottage Suite in the Upcountry of Maui!
Relaxing Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!
maui-hawaii_0052

Relaxing Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!

10.0 out of 10, Exceptional, (2)
"Exceeded our expectations! From the easy check-in to the incredible breakfasts, the old-school pool and hanging garden, and an unexpected herd of deer running through the property, this was one of the most relaxing and tranquil escapes we’ve experienced. The town of Makawao gave us tasty afternoon meals (Satori!) and the beautiful mountain area provided plenty of scenic driving. Only advice I’d give is to plan to enjoy the space while you’re staying, as it would be a shame to not settle in....
Relaxing Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!
Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!
hoku-large

Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!

10.0 out of 10, Exceptional, (6)
"Great property & location, excellent hosts!"
Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!
Modern Upcountry Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!
maui-hawaii_0081

Modern Upcountry Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!

2.0 star property
10.0 out of 10, Exceptional, (1)
"We stayed 3 nights. This was the first time to stay upcountry and we were pleasantly surprised by the contrast of the slower pace from the beach areas. Greeted with a smile by Josh as we came to the entry door and he explained about check in. The house is newly renovated, welcoming and very clean all over. The suite is huge, comfortable and private. Shower has plenty of hot water and pressure. We had lovely and tasty breakfast with some items changed every day. Josh will make Latte on request....
Modern Upcountry Hawaiian Suite for a Romantic Getaway in the Upcountry of Maui!
Kalani
Open plan living room looking out over the huge back yard down to the ocean.

Kalani

The price is AED 1,282
AED 2,640 total
includes taxes & fees
24 Feb - 25 Feb
Kalani
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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Other property types in Upcountry Maui

Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3450)
"We had a great stay at this beautiful property. Enjoyed watching the whales from our balcony. Highly recommend! "
The price is AED 1,429
AED 1,794 total
includes taxes & fees
27 Feb - 28 Feb
Aston Kaanapali Shores
OUTRIGGER Honua Kai Resort & Spa
Exterior

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2691)
"Surf, whales, gracious staff, Beautifully landscaped We will definitely return to the Outrigger Hanoa Kai"
The price is AED 1,602
AED 3,835 total
includes taxes & fees
28 Feb - 1 Mar
OUTRIGGER Honua Kai Resort & Spa
Kaanapali Alii
Pool

Kaanapali Alii

4.0 star property
9.4 out of 10, Exceptional, (859)
"Beautiful accommodations."
Kaanapali Alii
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.

Frequently asked questions

How much do cottages in Upcountry Maui cost?
Cottages in Upcountry Maui range between and per night. These retreats offer a chance to touch base with nature — at a price you can afford. 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?
Take your pick of cottages in Upcountry Maui. Whether you’re traveling with the family, as a duo or with a group of friends, Expedia makes it simple to find the ideal space.
Why book your cottage in Upcountry Maui with Expedia?
Expedia has some superb cottages in Upcountry Maui, so start packing your bags for an unforgettable vacation on nature’s doorstep. If you need to stick to a budget, choose how much you want to spend and your preferred property star rating. Or, try out our filters to search for cottages with a hot tub or a kitchen. We’ll help you find the right digs whatever your plans or bank balance.
How can I find cheap cottages in Upcountry Maui?
Expedia is here to help you track down cheap cottages in Upcountry Maui. To discover a superb stay in a couple of clicks, try out our handy filter tool to refine your search by budget, amenities and star rating.