Hot Upcountry Maui Cottage Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Cottages in Upcountry Maui

Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm

Hana
The price is AU$868 per night from 3 Dec to 4 Dec
AU$868
includes taxes & fees
3 Dec - 4 Dec
When you stay at this cottage in Hana, you'll be near the beach, within a 5-minute drive of Hana Lava Tubes and Kaʻeleku Caverns.
Secluded cottage on Tropical flower farm
Luxury  Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004

Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004

Kihei
With a stay at this cottage in Kihei (Wailea), you'll be within a 10-minute drive of Wailea Beach and Ulua Beach Park.
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
ALOHA DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub

ALOHA DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub

Haiku-Pauwela
Located in Haiku, this cottage is in a rural location, a 4-minute drive from Haleakala Bike Company and 8 minutes from Haiku Park.
ALOHA DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
Save an average of 15% on thousands of hotels when you're signed in
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Kihei
With a stay at this cottage in Kihei (Wailea), you'll be within a 15-minute drive of Wailea Beach and Ulua Beach Park.
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Cozy Maui 'Treehouse' with lovely views and amenities

Cozy Maui 'Treehouse' with lovely views and amenities

Kihei
With a stay at this cottage in Kihei, you'll be by the sea, within a 15-minute drive of Wailea Beach and Kihei Kalama Village.
Cozy Maui 'Treehouse' with lovely views and amenities
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
The price is AU$796 per night from 25 Nov to 26 Nov
AU$796
includes taxes & fees
25 Nov - 26 Nov
Located in Hana, this cottage is in a rural location, within a 15-minute walk of Hana Coast Gallery and Hana Cultural Center.
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!

Cute Plantation Cottage; Walk into Wailuku Town; Central Location!

Wailuku
With a stay at this cottage, you'll be centrally located in Wailuku, just a 4-minute walk from Iao Theater and 9 minutes by foot from Kaʻahumanu Church.
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
Plantation Style cottage short walk to beach and town 
Permit STPH2013/0004

Plantation Style cottage short walk to beach and town Permit STPH2013/0004

Paia
A stay at this cottage places you in the heart of Paia, within a 10-minute walk of One Love Farmers Market and Lower Paia Park.
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
Great location between Hana Town and Hamoa Beach, private, family-friendly

Great location between Hana Town and Hamoa Beach, private, family-friendly

Hana
The price is AU$855 per night from 20 Dec to 21 Dec
AU$855
includes taxes & fees
20 Dec - 21 Dec
When you stay at this cottage in Hana, you'll be by the sea, within a 5-minute drive of Hana Coast Gallery and Hana Cultural Center.
Great location between Hana Town and Hamoa Beach, private, family-friendly
Don't see what you're looking for?
See all available properties in Upcountry Maui
View all properties
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.

Upcountry Maui Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Upcountry Maui will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Upcountry Maui definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Upcountry Maui, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Upcountry Maui Cottages essential information

Accommodation
22 Cottages
Lowest Price
AU$645
Highest Price
AU$1,076
Popular accommodation
Secluded cottage on Tropical flower farm, Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004, ALOHA DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub, Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted, Cozy Maui 'Treehouse' with lovely views and amenities, Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath, Cute Plantation Cottage; Walk into Wailuku Town; Central Location!, Plantation Style cottage short walk to beach and town Permit STPH2013/0004 , Great location between Hana Town and Hamoa Beach, private, family-friendly

Top trending hotels in Upcountry Maui

Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy, Lahaina, HI
Fully refundableReserve now, pay when you stay
The price is AU$688 per night from 8 Dec to 9 Dec
AU$688
includes taxes & fees
8 Dec - 9 Dec
When you stay at Aston Kaanapali Shores in Kaanapali, you'll be on the beach, within a 10-minute drive of Kaanapali Beach and Whalers Village.
Aston Kaanapali Shores
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is AU$1,076 per night from 4 Dec to 5 Dec
AU$1,076
includes taxes & fees
4 Dec - 5 Dec
With a stay at Fairmont Kea Lani Maui in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Wailea Blue Golf Course.
Fairmont Kea Lani Maui
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
2525 Kaanapali Parkway, Lahaina, HI
Fully refundableReserve now, pay when you stay
The price is AU$645 per night from 18 Dec to 19 Dec
AU$645
includes taxes & fees
18 Dec - 19 Dec
With a stay at OUTRIGGER Kaanapali Beach Resort in Kaanapali, you'll be on the beach, within a 10-minute walk of Kaanapali Beach and Black Rock.
OUTRIGGER Kaanapali Beach Resort
Save an average of 15% on thousands of hotels when you're signed in
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

4 out of 5
200 Nohea Kai Dr, Lahaina, HI
Fully refundableReserve now, pay when you stay
The price is AU$965 per night from 28 Nov to 29 Nov
AU$965
includes taxes & fees
28 Nov - 29 Nov
With a stay at Hyatt Regency Maui Resort & Spa in Kaanapali, you'll be on the beach, a 3-minute walk from Kaanapali Beach and a 3-minute drive from Whalers ...
Hyatt Regency Maui Resort & Spa
Don't see what you're looking for?
See all available properties in Upcountry Maui
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.