Upcountry Maui Vacations from $938

Book a Hotel + Flight or Car together to unlock savings

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.
Lahaina Shores Beach Resort By Castle

Lahaina Shores Beach Resort By Castle

Save 100% on your flight
$938
per person
Sep 16 - Sep 21
found 24 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
No reviews
Wailea Beach Villas

Wailea Beach Villas

Wailea
Save 100% on your flight
$1,978
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

Maui Beach Vacation Club

North Kihei
Save 100% on your flight
$1,115
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.4/10 Very Good! (926 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

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
Save 100% on your flight
$1,668
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

South Kihei
$1,026
per person
Sep 28 - Oct 3
found 14 hours ago
Roundtrip non-stop flight included
Burbank (BUR) 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

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

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

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

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

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

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.
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

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.
See properties

Upcountry Maui Hotel Deals

Gods Peace Of Maui

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI
$167 nightly
$198 total
Aug 28 - Aug 29
Total with taxes and fees
Gods Peace Of Maui
Aston Kaanapali Shores

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy Lahaina HI
Fully refundableReserve now, pay when you stay
$269 nightly
$320 total
Aug 25 - Aug 26
Total with taxes and fees
8.8/10 Excellent! (4,250 reviews)
"Ideal for families! We are a family of 5, 3 teenagers. We could spend time as a family and had separate spaces for down time. The property is amazing! So beautiful! Two pool areas and the beach front offers much for fun and relaxation! Would return in a heartbeat!"

Reviewed on Aug 12, 2026

Aston Kaanapali Shores
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr Lahaina HI
Fully refundableReserve now, pay when you stay
$512 nightly
$608 total
Aug 14 - Aug 15
Total with taxes and fees
Hyatt Regency Maui Resort & Spa
See all 13,196 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.

Find the Best Upcountry Maui Vacation Packages

Upcountry Maui Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Kahului Airport (OGG)

More vacations you might like

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.