Upcountry Maui Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 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 easyPlan, book, and manage your trip all in one place
Find the Best Upcountry Maui Vacation Packages
Upcountry Maui Hotel Deals
Gods Peace Of Maui
1290 Haliimaile Rd Makawao HI
₩225,439
₩267,625 total
Oct 2 - Oct 3
includes taxes & fees
8.6/10 Excellent! (153 reviews)
"Simple and easy to stay. Parking in 5 seconds away, clean room and shower and toilet. Clean towels and blanket - thoughtfully placed. Kettle and microwave in the kitchen. Best beautiful and affordable place to stay."
Reviewed on Sep 29, 2026
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
₩990,362
₩1,263,526 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
"The property is gorgeous, on a wonderful beach, and has everything. We loved the waterslides, great restaurants, comfy beds, and beautiful sunsets. We will definitely be back!!"
Reviewed on Sep 30, 2026
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
₩266,548
₩379,321 total
Oct 27 - Oct 28
includes taxes & fees
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.
Stay near popular Upcountry Maui attractions
Haleakala Crater
9.6/10 (547 reviews)
One of the best places in the U.S. to watch the sunrise is this impressive centerpiece of Haleakalā National Park, marking the birthplace of the island of Maui.
Maui Spa Retreat
6.6/10 (4 reviews)
Enjoy a trip to Maui Spa Retreat and popular activities like surfing in Makawao. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.
Haleakalā Visitor Center
9.0/10 (2 reviews)
Explore the lovely green spaces of Haleakalā Visitor Center and enjoy the golf courses in Kula. Wander the beautiful beaches and seaside in this relaxing area.
Makawao Park
8.0/10 (2 reviews)
Explore the great outdoors at Makawao Park, a lovely green space in Makawao. Stroll along the area's seaside, or simply savor its top-notch restaurants.
Hoʻomana Spa Maui
You can take time to visit Hoʻomana Spa Maui during your travels to Makawao. Wander the beautiful beaches and seaside in the area.
Kula Botanical Garden
Enjoy the beautiful sunsets and explore Kula Botanical Garden, a lovely green space in Kula. Stroll along the area's seaside or experience its great live music.
Polipoli Spring State Recreation Area
Enjoy the beautiful sunsets and explore Polipoli Spring State Recreation Area, a lovely green space in Kula. Stroll along the beautiful beaches in this romantic area, or check out its top-notch restaurants.
Hosmer Grove
Explore the great outdoors at Hosmer Grove, a lovely green space in Kula. Stroll along the seaside in this relaxing area, or seek out the yoga studios.
Frequently asked questions
How much does an Upcountry Maui vacation package cost?
Perhaps less than you imagined — from a tempting , as a matter of fact! By combining flights, hotels and car rentals into your own custom-made vacation package, your getaway to Upcountry Maui is just clicks away.
How do I get a cheap travel package to Upcountry Maui?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and rental cars — we've got everything you need. Pick and choose the combination that suits you and watch your savings pile up. We know a travel package is never a one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 hotel options across the globe, which lets you customize your Upcountry Maui adventure.
What are the top hotels in Upcountry Maui?
When it comes to hotels in Spreckelsville, Paia Inn and Kaiholo Hale are two great options. If you're also spending time in Haliimaile, Private Lush 2 Acre Mountain Home Maui Permitted#stmp 2013 and Adorable 1930's Gingerbread House. . . . Permitted look forward to welcoming you.
How far in advance should I book my Upcountry Maui vacation?
It's always wise to book early. Air carriers generally release flight tickets up to a year in advance, and this is a great opportunity to land some rock-bottom prices. Boss just told you to take all your vacation days next week? No need to worry. Expedia are never short on fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Upcountry Maui travel package include?
With Expedia, you can choose any combination of car rentals, hotels and flights to create your ideal Upcountry Maui travel package. Once you've made your booking, you can add on the fun things like sightseeing tours and activities. Remember, the more you bundle, the bigger the savings!
What should I know before booking an Upcountry Maui travel package?
A travel package can be easier on the wallet than individually booking all you need for your getaway. For example, combine your hotels, flights and rental cars and score impressive savings. No matter your vacation goals, you're bound to find a package to suit your budget.
Can I choose my airline with an Upcountry Maui Expedia vacation package?
Yes, of course. We have more than 550 airline partners all over the world, so pick the carrier that matches your needs.
If I'm not able to travel, can I cancel my Upcountry Maui vacation package?
Plans can change suddenly, so yes, you can. You may be able to cancel or amend your Upcountry Maui vacation package at no cost within 24 hours of booking. For bookings older than that, you can still cancel and rebook, but your car rental company, hotel or airline may charge a fee. Need more information? Have a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
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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.
