Upcountry Maui Vacation Packages 2026 from $744

Upcountry Maui flight + hotel vacation packages

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

Kahana Beach Vacation Club

Save 100% on your flight

$744

per person

Feb 19 - Feb 22

found 18 hours 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

$2,679

per person

Jan 19 - Jan 26

found 19 hours 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.

Maui Banyan Vacation Club

South Kihei

Save 100% on your flight

$1,032

per person

Feb 21 - Feb 27

found 22 hours 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.

The Gardens at West Maui

Save 100% on your flight

$779

per person

Feb 19 - Feb 22

found 18 hours 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.

The Whaler Resort Kaanapali Beach

$1,950

per person

Feb 10 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

This condo's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, a garden, and a picnic area are also on offer.

Top Upcountry Maui hotels deals

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

$155 nightly

$183 total

Dec 15 - Dec 16

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

$489 nightly

$577 total

Dec 16 - Dec 17

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

$229 nightly

$270 total

Dec 14 - Dec 15

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

Maui Coast Hotel

2259 S Kihei Rd Kihei HI

Free Cancellation

Reserve now, pay when you stay

$254 nightly

$301 total

Jan 8 - Jan 9, 2026

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

OUTRIGGER Kaanapali Beach Resort

2525 Kaanapali Parkway Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$292 nightly

$344 total

Dec 16 - Dec 17

Total with taxes and fees

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

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$700 nightly

$826 total

Dec 11 - Dec 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

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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.

Lavender farms up in Kula 💜 #maui #lavenderfarm

Aliʻi Kula Lavender

Find out about the history of Kula when you spend time at Aliʻi Kula Lavender. Stroll along the beautiful beaches in this romantic area, or seek out the snorkeling spots.

Frequently asked questions

How much are vacation packages to Upcountry Maui?

With deals starting at just $744, 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.