Upcountry Maui Vacation Packages 2026 from $1,314

Name: Royal Lahaina Resort & Bungalows
Price range: $384 total

Upcountry Maui flight + hotel vacation packages

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

OUTRIGGER Kaanapali Beach Resort

Save 100% on your flight

$1,314

per person

Apr 16 - Apr 22

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

This resort features a restaurant, an outdoor pool, and a bar/lounge. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Guests will appreciate perks like free WiFi and a free area shuttle.

Kahana Beach Vacation Club

$1,648

per person

Apr 16 - Apr 22

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. Laundry facilities, concierge services, and barbecue grills are also on offer.

Sands of Kahana

Save 100% on your flight

$2,949

per person

Apr 16 - Apr 22

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

This aparthotel features an outdoor pool and a gym. Enjoy the outdoor tennis court and perks like free self parking. A garden, laundry facilities, and concierge services are also on offer.

OUTRIGGER Honua Kai Resort & Spa

Save 100% on your flight

$2,101

per person

Apr 18 - Apr 24

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

4 outdoor pools, a lazy river, and a gym are all featured at this luxury condo resort. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the convenience store. Enjoy a meal from the a restaurant and perks like free valet parking.

Kahana Villa

$1,420

per person

May 21 - May 26

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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. Laundry facilities and barbecue grills are also provided.

Top Upcountry Maui hotels deals

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

$152 nightly

$181 total

Mar 18 - Mar 19

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

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$705 nightly

$837 total

Apr 12 - Apr 13

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

$324 nightly

$384 total

Mar 29 - Mar 30

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

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$716 nightly

$850 total

Apr 11 - Apr 12

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

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$1,150 nightly

$1,365 total

Mar 16 - Mar 17

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

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$1,214 nightly

$1,441 total

Mar 15 - Mar 16

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.

Pool

Hot Tub

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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.

The grounds and main building are beautiful. It's a great place to walk around and admire the beauty. Check website for exhibit information. http://huinoeau.com #Hawaii #Makawao #Maui #UnitedStates #USA #Art #MonkeyPodTree #architecture

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 $1,314, 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.