Upcountry Maui Vacation Packages 2026 from $1,138

Name: Royal Lahaina Resort & Bungalows
Price range: $326 total

Upcountry Maui flight + hotel vacation packages

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

Kihei Kai Nani

South Kihei

$1,138

per person

Sep 15 - Sep 22

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Kahului (OGG)

An outdoor pool, free self parking, and concierge services are featured at this condo. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.

Maui Beach Vacation Club

North Kihei

Save 100% on your flight

$1,282

per person

Sep 16 - Sep 23

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

Save 100% on your flight

$2,176

per person

Sep 16 - Sep 22

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 business center, laundry service, and valet parking. Unwind with a drink at the poolside bar and enjoy perks like a free beach shuttle.

Palms at Wailea Maui

Wailea

Save 100% on your flight

$1,537

per person

Sep 17 - Sep 22

found 14 hours ago

Roundtrip flight included

Los Angeles (LAX) 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.

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

$2,756

per person

Sep 15 - Sep 22

found 1 day 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

$185 nightly

$220 total

Jul 6 - Jul 7

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.

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$865 nightly

$1,027 total

Jul 17 - Jul 18

Total with taxes and fees

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$528 nightly

$626 total

Jul 19 - Jul 20

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.

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$274 nightly

$326 total

Jul 19 - Jul 20

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.

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$1,099 nightly

$1,305 total

Jul 30 - Jul 31

Total with taxes and fees

A full-service spa, 6 restaurants, and 3 outdoor pools are all featured at this luxury resort. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities.

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr Lahaina HI

$576 nightly

$684 total

Jul 7 - Jul 8

Total with taxes and fees

This resort features a golf course, a full-service spa, and 4 restaurants. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the 6 outdoor pools and gym, and unwind with a drink at the poolside bar.

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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 $1,138, 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.