Upcountry Maui Vacation Packages 2026 from $564

Upcountry Maui flight + hotel vacation packages

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

The Gardens at West Maui

$564

per person

Apr 14 - Apr 17

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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, luggage storage, and barbecue grills are also on offer.

Hono Koa Vacation Club

Save 100% on your flight

$1,263

per person

Apr 18 - Apr 25

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Kahului (OGG)

An outdoor pool, free self parking, and barbecue grills are featured at this condo. WiFi in public areas is free. A garden is also provided.

Kahana Beach Vacation Club

Save 100% on your flight

$751

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Maui Beach Vacation Club

North Kihei

Save 100% on your flight

$2,106

per person

Apr 18 - Apr 25

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.

Maui Parkshore - Maui Condo & Home

South Kihei

Save 100% on your flight

$1,452

per person

Mar 31 - Apr 7

found 19 hours ago

Roundtrip flight included

Los Angeles (LAX) to Kahului (OGG)

An outdoor pool is featured at this condo, along with a garden and a picnic area. Laundry facilities and barbecue grills are also provided.

Top Upcountry Maui hotels deals

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

$167 nightly

$198 total

Feb 11 - Feb 12

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

$538 nightly

$638 total

Feb 7 - Feb 8

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

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$850 nightly

$1,009 total

Feb 11 - Feb 12

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

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$337 nightly

$400 total

Feb 25 - Feb 26

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

$763 nightly

$905 total

Feb 8 - Feb 9

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

Maui Coast Hotel

2259 S Kihei Rd Kihei HI

Free Cancellation

Reserve now, pay when you stay

$299 nightly

$355 total

Feb 10 - Feb 11

Total with taxes and fees

This hotel features 2 outdoor pools, 3 hot tubs, and a restaurant. Enjoy the 24-hour gym and perks like free WiFi and a free area shuttle. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.

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

You can spend time browsing the exhibits at Hui Noʻeau Visual Arts Center during your travels in Makawao. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

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 $564, 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.