Upcountry Maui Romantic Holidays

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    Packages 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

HOOKIPA BAYVIEW COTTAGE Private, Romantic Maui Cottage, in Haiku
HOOKIPA BAYVIEW COTTAGE Private, Romantic Maui Cottage, in Haiku
Haiku-Pauwela, HI
  • 34 min drive from Haleakala National Park
Stay at this cottage in Haiku. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Haleakala Bike Company and Haiku Park are located ...
10/10 Exceptional! (161 reviews)

Couples like: adults-only property, Hot tub

Another Relaxing Getaway
"Our fourth visit to the cottage and we’re always thrilled with our vacations here. Hank is a gracious host and we love the peace and quiet of this secluded north shore gem. We’ll definitely be back!"

Reviewed on 16 May 2025

HOOKIPA BAYVIEW COTTAGE Private, Romantic Maui Cottage, in Haiku
Adorable 1930's Gingerbread House....Permitted!
Adorable 1930's Gingerbread House....Permitted!
Makawao, HI
  • 29 min drive from Haleakala National Park
Stay at this family-friendly cottage in Makawao. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Hui Noʻeau Visual Arts Center and Enlighten ...
9.6/10 Exceptional! (11 reviews)
"a beautiful property and a nice cottage! We completely enjoyed our time here."

Reviewed on 5 Jun 2025

Adorable 1930's Gingerbread House....Permitted!
Bamboo Valley Inn
Bamboo Valley Inn
3.5 out of 5
1444 West Kuiaha Rd, Haiku, HI
  • 33 min drive from Haleakala National Park
Stay at this 3.5-star B&B in Haiku. Enjoy free Wi-Fi, 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

Bamboo Valley Inn
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.

More holidays you might like

* 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.