
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
Price was CA $5,250, price is now CA $3,240 per person
CA $3,240
per person
Aug 9 - Aug 15
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
9.4/10 Exceptional! (1,003 reviews)
Everything was Amazing!! Will be coming back
Reviewed on Apr 18, 2026

Hampton Inn & Suites Maui North Shore
Price was CA $3,687, price is now CA $2,352 per person
CA $2,352
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9.2/10 Wonderful! (235 reviews)
The staff was very friendly, the rooms were clean with gorgeous views! The connected beach was nice to stroll down as well
Reviewed on May 12, 2026

Palms at Wailea Maui
Wailea
Price was CA $4,194, price is now CA $2,856 per person
CA $2,856
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
8.4/10 Very Good! (539 reviews)
Twin room had dirty sheets and place was swarmed with mosquitos.
Reviewed on May 2, 2026

Wailea Beach Resort - Marriott, Maui
Wailea
Price was CA $6,033, price is now CA $4,293 per person
CA $4,293
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9.2/10 Wonderful! (1,000 reviews)
The location is amazing and property has everything you need without ever leaving
Reviewed on May 22, 2026
Upcountry Maui Hotel Deals

Gods Peace Of Maui
1290 Haliimaile Rd Makawao HI
The price is CA $256 per night from May 27 to May 28
CA $256
CA $303 total
May 27 - May 28
includes taxes & fees
8.8/10 Excellent! (110 reviews)
"Hot tub was broken and seems to have been for awhile, obviously this is an important feature to be missing. Some of the extras like chairs and umbrellas are not in great condition, although they were nice to have. The breakfast offerings were fine although I wouldn't call it a bed and breakfast. ..."
Reviewed on May 19, 2026

The Westin Maui Resort & Spa, Ka'anapali
2365 Kaanapali Pkwy Lahaina HI
Fully refundableReserve now, pay when you stay
The price is CA $673 per night from May 30 to May 31
CA $673
CA $879 total
May 30 - May 31
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Excellent property. Has all the amenities you can imagine. On the beach great walk/run paths. Will definitely stay here again."
Reviewed on May 22, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
The price is CA $1,283 per night from Jun 14 to Jun 15
CA $1,283
CA $1,612 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Impeccable! Tess at Loulu was incredible so was Joseph during check in. I can’t wait to return"
Reviewed on May 22, 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.
Discover the most popular places to visit in Upcountry Maui

Haleakala Crater
4.5/5(77 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.
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- Garden of Eden Arboretum
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- All inclusive Vacation Packages Maui
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







