Upcountry Maui Vacation Packages 2026 from $1,471

Upcountry Maui flight + hotel vacation packages

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

Kapalua Villas Maui

$1,471

per person

Jun 15 - Jun 21

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Kahului (OGG)

This smoke-free aparthotel features 8 restaurants, 3 outdoor pools, and 2 outdoor tennis courts. A garden, a picnic area, and barbecue grills are also on offer.

Palms at Wailea Maui

Wailea

$2,458

per person

Jun 28 - Jul 5

found 8 hours ago

Roundtrip flight included

Dallas (DFW) to Kahului (OGG)

This aparthotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Wailea Grand Champions - Maui Condo & Home

Wailea

$1,612

per person

Jun 1 - Jun 8

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Kahului (OGG)

5 outdoor tennis courts, an outdoor pool, and a hot tub are all featured at this smoke-free condo. Barbecue grills are provided for your convenience.

The Ritz-Carlton Maui, Kapalua

$1,636

per person

May 15 - May 18

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Kahului (OGG)

This luxury resort features a golf course, a full-service spa, and 6 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities.

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

$4,328

per person

Jun 28 - Jul 5

found 24 hours ago

Roundtrip flight included

Dallas (DFW) to Kahului (OGG)

A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, children's pool, and waterslide.

Top Upcountry Maui hotels deals

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

$154 nightly

$182 total

Apr 23 - Apr 24

Total with taxes and fees

A full-service spa, free self parking, and barbecue grills are featured at this bed & breakfast. Guests will appreciate free perks like self-serve breakfast and WiFi in public areas. A garden, a library, and a picnic area are also on offer.

Breakfast included

Spa

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$315 nightly

$374 total

May 4 - May 5

Total with taxes and fees

This hotel features a full-service spa, 2 outdoor pools, and 11 outdoor tennis courts. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a shopping center shuttle.

Pool

Spa

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$486 nightly

$577 total

May 8 - May 9

Total with taxes and fees

A full-service spa, 2 restaurants, and 3 outdoor pools are all featured at this luxury hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Bring the family and enjoy the children's club, waterslide, and kid-friendly dining.

Pool

Hot Tub

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$716 nightly

$850 total

May 6 - May 7

Total with taxes and fees

Pool

Hot Tub

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$765 nightly

$908 total

Apr 30 - May 1

Total with taxes and fees

A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a free kid's club and a children's pool, and free supervised childcare is an added bonus.

Pool

Hot Tub

Maui Seaside Hotel

100 W Kaahumanu Ave Kahului HI

Free Cancellation

Reserve now, pay when you stay

$237 nightly

$282 total

Apr 27 - Apr 28

Total with taxes and fees

A restaurant and an outdoor pool are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas and free airport shuttle. Self parking and luggage storage are also offered on site.

Pool

Free airport shuttle

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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.

Popular places to visit

Haleakala Crater

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.

Hui Noʻeau Visual Arts Center

Enjoy an outing to Hui Noʻeau Visual Arts Center during your stay in Makawao. Wander the beautiful beaches and seaside in the area.

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.

Frequently asked questions

How much are vacation packages to Upcountry Maui?

With deals starting at just $1,471, flight and hotel packages are a superb way to stretch your vacation budget. Upcountry Maui, here you come!

Where can I get the best vacation package deals for Upcountry Maui?

There's no need to look any further than Travelocity. With no less than 400 partner airlines and 1,000,000 worldwide properties, it's easy to find an Upcountry Maui package deal that suits your needs.

Why should I book my Upcountry Maui vacation package with Travelocity?

Nothing beats the peace of mind knowing you've scored the best price in town — that's our Price Match Guarantee. Add to that our fantastic range of destinations and 24/7 team of customer service professionals and you've got the formula for an unforgettable vacation.

Can I save on my Upcountry Maui car rental if I book it with hotels and flights?

Combining your bookings into an Upcountry Maui vacation package will leave you with a nice chunk of spare change. You can choose a car and flight; a car, hotel and flight; or a hotel and car. You won't find a better way to discover the greater Upcountry Maui region than from the comfort of your own rental car. You can also add activities and experiences to your Travelocity package.

Which airport is best for Upcountry Maui?

Kahului Airport (OGG) is where many people choose to touch down. Depending on where you're going in Upcountry Maui, Molokai Airport (MKK) and Lanai Airport (LNY) are also worth considering.

What is there to do in Upcountry Maui?

You'll be happy to know Upcountry Maui is teeming with fabulous things to see and do, however Haleakala National Park and Hookipa Beach Park are right up there with the very best.