Upcountry Maui Romantic Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Romantic Upcountry Maui Hotels
HOOKIPA BAYVIEW COTTAGE Private, Romantic Maui Cottage, in Haiku
Haiku-Pauwela
Stay at this cottage in Haiku. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Haleakala Bike Company and Haiku Park are located ...
10/10 Exceptional! (165 reviews)
"Another magical stay at my happy place. From the moment you pull up to the cottage to the moment you turn off the lights at night, Hank's place will lull you into a state of calm you’ve never experienced before. With all you need for a most comfortable stay with a view you can’t wait to wake up to ..."
Reviewed on 14 Sept 2025
Adorable 1930's Gingerbread House....Permitted!
Makawao
Book a stay at this family-friendly cottage in Makawao. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Hui Noʻeau Visual Arts Center ...
9.6/10 Exceptional! (12 reviews)
"Amazing time in Makawao! The property is beautiful, private and has an authentic Hawaii feel. The Gingerbread house was super clean and bed/linens cozy. The hosts are welcoming and have great recommendations. Loved our stay—new favorite place on Maui."
Reviewed on 18 Sept 2025
Bamboo Valley Inn
1444 West Kuiaha Rd, Haiku, HI
Stay at this 3.5-star B&B in Haiku. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Haleakala Bike Company and Hui Noʻeau Visual Arts ...
"I recently stayed at Bamboo Valley Inn, and while I had high hopes based on its charming description, my experience fell short in several areas. First, I was disappointed to find that the claim of “breakfast included” was misleading. Upon arrival, I learned that no breakfast was provided, which was ..."
Reviewed on 3 Jan 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
