Upcountry Maui Vacation Packages
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Top Upcountry Maui Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
CA $4,528
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
Everything was excellent, form the location to the incredible food!
Reviewed on Sep 22, 2026
Maui Beach Vacation Club
North Kihei
CA $2,208
per person
Nov 8 - Nov 13
found 23 hours ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
8.4/10 Very good! (937 reviews)
The property was in a great location, close to many shops and the beach. It was easy to get around, and we especially enjoyed walking along the beach. Although there was no air conditioning, it was a lovely property overall, and we really enjoyed our stay!
Reviewed on Sep 25, 2026
Ready to book your vacation to Upcountry Maui?
Upcountry Maui Hotel Deals
Gods Peace Of Maui
1290 Haliimaile Rd Makawao HI
CA $235
CA $279 total
Sep 30 - Oct 1
includes taxes & fees
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
CA $1,139
CA $1,444 total
Oct 9 - Oct 10
includes taxes & fees
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
CA $273
CA $389 total
Sep 30 - Oct 1
includes taxes & fees
9.6/10 Exceptional! (2,689 reviews)
"We had a beautiful ocean view from our room. Loved the pools but too much chlorine. The cocktails at the bar were really bad."
Reviewed on Sep 25, 2026
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.
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.
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.
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 CA $1,808, 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.
Explore a world of travel with Expedia
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- Condo Rentals in Kihei
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- Hotels near Kahului
- Hostels in Maui
- Honeymoon Resorts and in Maui
- Exceptional Ocean Views
- Hana Hotels
- Flights to Maui
- Flights from Los Angeles (LAX) to Kahului (OGG)
- Flights from Maui
- Flights from Honolulu (HNL) to Kahului (OGG)
- Flights from Edmonton (YEG) to Kahului (OGG)
- Flights from Toronto (YYZ) to Kahului (OGG)
- Flights from Calgary (YYC) to Kahului (OGG)
- Flights from Vancouver (YVR) to Kahului (OGG)
- Flights from Victoria (YYJ) to Kahului (OGG)
- Flights from Kahului
- Haleakala Crater
- Waipuilani Park
- All inclusive Vacation Packages Maui
- Kahului Vacations
- Maui Nui Botanical Gardens
- Kamaole Beach Park 3
- Wailea Blue Golf Course
- Wailea Beach
- Ahihi Kinau Natural Area Reserve
- Visit Maui
- Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters
- Molokini
- Haleakala National Park
- Keawakapu Beach North
- Hana Vacations
- Hamoa Beach
- Makena State Park Beach
- Kokomo Vacations
- Koki Beach Park
- Hoʻokipa Beach Park
- Kihei Vacations
- Visit Upcountry Maui
- Paia Vacations
- Kuau Bay Beach
- Kamaole Beach Park 2
- Makena Vacations
- Garden of Eden Arboretum
- Iao Valley State Park
- Maluaka Beach
- Wailea Vacations
- Oneuli Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
