Upcountry Maui Vacation Packages 2026 from $890

Upcountry Maui flight + hotel vacation packages

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

Lahaina Shores Beach Resort By Castle

Save 100% on your flight

$890

per person

Oct 15 - Oct 20

found 5 hours ago

Roundtrip flight included

Los Angeles (LAX) to Kahului (OGG)

An outdoor pool, self parking, and laundry facilities are featured at this apartment. The front desk is staffed around-the-clock and barbecue grills are on offer.

Maui Beach Vacation Club

North Kihei

Save 100% on your flight

$1,395

per person

Oct 1 - Oct 8

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A garden and barbecue grills are also provided.

Maui Banyan Vacation Club

South Kihei

Save 100% on your flight

$1,039

per person

Oct 1 - Oct 8

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

This condo features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, concierge services, and barbecue grills are also on offer.

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

$3,147

per person

Oct 10 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Kahului (OGG)

This luxury resort includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the laundry service, conference center, and valet parking. A free beach shuttle is offered as well.

Mana Kai Maui- Official Onsite Rental

South Kihei

Save 100% on your flight

$1,070

per person

Oct 1 - Oct 8

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a garden, and a grocery/convenience store are also offered.

Top Upcountry Maui hotels deals

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

$185 nightly

$220 total

Jul 31 - Aug 1

Total with taxes and fees

This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. Enjoy the free self-serve breakfast each morning. A garden, a library, and a picnic area are also on offer.

Breakfast included

Pet friendly

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$255 nightly

$303 total

Aug 9 - Aug 10

Total with taxes and fees

A full-service spa, 2 outdoor pools, and 2 outdoor tennis courts are featured at this smoke-free aparthotel. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 hot tubs and perks like free WiFi.

Pool

Hot Tub

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$786 nightly

$933 total

Aug 16 - Aug 17

Total with taxes and fees

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.

Pool

Hot Tub

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$651 nightly

$772 total

Aug 21 - Aug 22

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

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$292 nightly

$347 total

Aug 30 - Aug 31

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 Ritz-Carlton Maui, Kapalua

1 Ritz-Carlton Drive Kapalua HI

$858 nightly

$1,019 total

Jul 31 - Aug 1

Total with taxes and fees

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.

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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.

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

Frequently asked questions

How much are vacation packages to Upcountry Maui?

With deals starting at just $890, 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.