Upcountry Maui Vacation Packages 2026 from $915

Photo by Project Forever

Plan, book, travel with confidence
Better together
Save up to $2,000 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

The Latest Upcountry Maui vacation packages

Price found within the past 48 hours. Click for updated prices.

Maui Beach Vacation Club

North Kihei

Save 100% on your flight

$915

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

8.4/10 Very Good! (933 reviews)

Wailea Beach Villas

Wailea

Save 100% on your flight

$1,929

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

9.8/10 Exceptional! (199 reviews)

The Kalama Residence

South Kihei

Save 100% on your flight

$3,431

per person

Oct 28 - Nov 4

found 1 hour ago

Roundtrip flight included

Los Angeles (LAX) to Kahului (OGG)

8/10 Very Good! (3 reviews)

The property was clean and nice. It did need some maintenance, but it was in good condition for its age. We liked how it was stocked to make our stay more comfortable.

Reviewed on Jan 4, 2026

Maui Banyan Vacation Club

South Kihei

Save 100% on your flight

$927

per person

Sep 28 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

8/10 Very Good! (385 reviews)

Check in was smooth, Rooms were a lot smaller then when looking to book. Air conditioning did not see to work right. Room fan also did not work right, bed was not as comfortable

Reviewed on Aug 22, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

Save 100% on your flight

$2,691

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

9.4/10 Exceptional! (1,004 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Upcountry Maui

View all trips

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.

See properties

Maui Agricultural Research Center

Find out about the history of Kula when you spend time at Maui Agricultural Research Center. In the area, take in the great live music and beautiful sunsets.

See properties

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 romantic area.

See properties

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.

See properties

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.

See properties

Hanawi Natural Forest Reserve

10.0/10 (1 review)

Commune with nature and explore the great outdoors at Hanawi Natural Forest Reserve during your travels in Hana. Discover the sunrises in this romantic area, or seek out the yoga studios.

See properties

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 seaside in this romantic area, or check out its seafood restaurants.

See properties

Kula Botanical Garden

Enjoy the beautiful sunsets and explore Kula Botanical Garden, a lovely green space in Kula. Stroll along the area's beautiful beaches or experience its great live music.

See properties

Upcountry Maui Hotel Deals

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

$195 nightly

$231 total

Sep 2 - Sep 3

Total with taxes and fees

8.6/10 Excellent! (142 reviews)

"Beautiful grounds. Had a "youth hostle" feel. No frills what so ever and all the rooms shared a bathroom. Nothing in the bedrooms except a bed. Common kitchen area and sitting area. Also lots of religious influence decor, books, and pamphlets. We never saw the owners and didn't feel free just to ..."

Reviewed on Aug 21, 2026

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr Lahaina HI

Fully refundableReserve now, pay when you stay

$504 nightly

$599 total

Aug 27 - Aug 28

Total with taxes and fees

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy Lahaina HI

Fully refundableReserve now, pay when you stay

$229 nightly

$272 total

Aug 27 - Aug 28

Total with taxes and fees

8.8/10 Excellent! (4,278 reviews)

"Overall, staff was very friendly! Shout out to the female concierge! She is hilarious and knows how to deliver a good time. The two outdoor pools are gorgeous especially at night with the beachfront view. If you’re on a budget, I highly recommend. It is definitely an older establishment and the cleanliness ..."

Reviewed on Aug 24, 2026

See all 13,271 properties in Upcountry Maui

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.