Upcountry Maui Vacation Packages 2025/2026 from $747

Upcountry Maui flight + hotel vacation packages

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

The Gardens at West Maui

per person

Aug 28 - Aug 31

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, luggage storage, and barbecue grills are also on offer.

Hono Koa Vacation Club

Save 100% on your flight

per person

Aug 28 - Sep 2

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) 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.

Maui Banyan Vacation Club

Save 100% on your flight

per person

Sep 2 - Sep 9

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.

Kahana Beach Vacation Club

Save 100% on your flight

per person

Sep 17 - Sep 21

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.

Mana Kai Maui- Official Onsite Rental

Save 100% on your flight

per person

Aug 28 - Aug 31

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

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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

Maui Coast Hotel

2259 S Kihei Rd, Kihei, HI

Free Cancellation

Reserve now, pay when you stay

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

Pool

Hot Tub

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy, Lahaina, HI

Free Cancellation

Reserve now, pay when you stay

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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

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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

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Kihei, HI

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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

OUTRIGGER Kaanapali Beach Resort

2525 Kaanapali Parkway, Lahaina, HI

Free Cancellation

Reserve now, pay when you stay

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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.

Pool

Pet friendly

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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

5/5(343 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.

When the sun was finally arising at Haleakala it's the breathtaking moment for such a wonderful view.

Haleakalā Visitor Center

Explore the lovely green spaces of Haleakalā Visitor Center and enjoy the golf courses in Kula. Wander the beautiful beaches and seaside in this romantic area.

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.

Frequently asked questions

How much are vacation packages to Upcountry Maui?

With deals starting at just $747, 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.