
Upcountry Maui Romantic Holidays
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £335 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
How to find a romantic Upcountry Maui holiday
How can I find the best Upcountry Maui vacation packages for couples?
Use our easy-to-use holiday search tools to plan your most-romantic getaway to Upcountry Maui. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.
Can I book cheap Upcountry Maui romantic holidays for two?
Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Upcountry Maui that start from . Prices and availability are subject to change. Additional terms may apply.
What should I think about when booking a Upcountry Maui romantic getaway?
The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.
What should I look for in a luxury romantic holiday to Upcountry Maui?
Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.
Can I book a romantic hot-tub holiday in Upcountry Maui?
What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.
How can I find romantic holidays for couples in Upcountry Maui that are all inclusive?
Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.
Can I book a romantic trip to Upcountry Maui with free cancellation and/or flexible dates?
Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.
Why should I book my Upcountry Maui romantic holiday with Expedia?
At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.
Top Romantic Upcountry Maui Hotels

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

PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!
Our host was the BEST! The property grounds were truly special. We were even lucky enough to join a moonlight walk along the labyrinth. Great communication and we were treated like family. Would stay here again a thousand times over.
Reviewed on 28 Jan 2026
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.










