Upcountry Maui Vacation Packages 2026 from $883

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The Latest Upcountry Maui vacation packages

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

Maui Banyan Vacation Club

South Kihei

Save 100% on your flight

$883

per person

Sep 15 - Sep 21

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Kahului (OGG)

8/10 Very Good! (382 reviews)

Excellent property, check-in/out was easy (they let me check in early), great location, parking extremely easy every day. Only thing to plan for that is different from some other rentals: don’t expect anything to already be in the kitchen as far as foo/spices/condiments or things like that. Some places will at least have salt & pepper non-perishable essentials like that, maybe umbrellas or chairs, this place did not so do just be prepared to bring everything you plan to need (bathroom has the basics though: shampoo/conditioner, soap, towels etc.). Great stay, very satisfied and would more than happily repeat.

Reviewed on Aug 3, 2026

Wailea Beach Villas

Wailea

Save 100% on your flight

$1,923

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

9.8/10 Exceptional! (197 reviews)

Luxury condo right on Wailea beach with restaurants and shops nearby. I loved the beach view adult only pool, and that it was crowded.

Reviewed on Jul 31, 2026

Maui Beach Vacation Club

North Kihei

Save 100% on your flight

$1,347

per person

Sep 16 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

8.4/10 Very Good! (922 reviews)

Must admit when we arrived and found there was no AC was a little worried, but the orientation of the unit meant the breezes blowing through made it just lovely. The beach was literally just over the road and super calm. Pool was great, location great for Kīhei Lahaina and the airport. Really enjoyed our stay

Reviewed on Aug 8, 2026

Lahaina Shores Beach Resort By Castle

$981

per person

Sep 16 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

No reviews

Wailea Grand Champions - Maui Condo & Home

Wailea

Save 100% on your flight

$1,554

per person

Sep 10 - Sep 17

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Kahului (OGG)

7.8/10 Good! (20 reviews)

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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.

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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.

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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.

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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.

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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.

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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.

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Pukalani Country Club

Play a round of golf in Pukalani at Pukalani Country Club, and enjoy other activities such as surfing. Stroll along the area's beautiful beaches or experience its great live music.

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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.

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Upcountry Maui Hotel Deals

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

$165 nightly

$196 total

Aug 20 - Aug 21

Total with taxes and fees

8.8/10 Excellent! (138 reviews)

"We loved the little studio cabin for our family of three for a few nights before we headed to Hana. Great jumping off spot for doing the sunrise at the mountain as well, was the closest I could find not in the park at a reasonable price. Bathroom is in a separate building that you have to walk to, ..."

Reviewed on Aug 7, 2026

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy Lahaina HI

Fully refundableReserve now, pay when you stay

$259 nightly

$307 total

Aug 20 - Aug 21

Total with taxes and fees

8.8/10 Excellent! (4,243 reviews)

"Room was outdated and dirty. Second to last day a cockroach fell down from the cabinet. We traveled with a big group and they seemed to have cleaner room. It’s sits on a great location for shopping and eatery but the beach is next to the runoff. For being our first time in Maui we definitely learned ..."

Reviewed on Aug 8, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$786 nightly

$933 total

Aug 22 - Aug 23

Total with taxes and fees

8.8/10 Excellent! (1,007 reviews)

"They did a wonderful job I was well taken care of at all times"

Reviewed on Aug 7, 2026

See all 13,264 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.