Upcountry Maui Vacation Packages 2026 from $2,248

Upcountry Maui flight + hotel vacation packages

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

Maui Kamaole - Maui Condo & Home

South Kihei

Save 100% on your flight

$2,248

per person

Jan 3 - Jan 9

found 1 day ago

Roundtrip flight included

Seattle (SEA) to Kahului (OGG)

2 outdoor pools, 4 outdoor tennis courts, and a hot tub are among this condo's featured amenities. A garden, a picnic area, and laundry facilities are also on offer.

Hotel Wailea Maui

Wailea

$5,260

per person

Dec 29 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Kahului (OGG)

This luxury resort includes 3 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free beach shuttle.

Maui Banyan Vacation Club

South Kihei

$2,324

per person

Dec 27 - Jan 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Maui Banyan - Maui Condo & Home

South Kihei

Save 100% on your flight

$2,256

per person

Jan 3 - Jan 9

found 1 day ago

Roundtrip flight included

Seattle (SEA) to Kahului (OGG)

2 outdoor pools, an outdoor tennis court, and a hot tub are all featured at this smoke-free condo. A picnic area and barbecue grills are also provided.

Grand Champions

Wailea

Save 100% on your flight

$2,828

per person

Jan 3 - Jan 9

found 1 day ago

Roundtrip flight included

Seattle (SEA) to Kahului (OGG)

This resort features an outdoor pool and a hot tub. Free self parking, a terrace, and a garden are also offered.

Top Upcountry Maui hotels deals

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

$152 nightly

$180 total

Oct 25 - Oct 26

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.

Breakfast included

Pet friendly

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$240 nightly

$285 total

Oct 30 - Oct 31

Total with taxes and fees

A full-service spa, 2 outdoor pools, and 2 outdoor tennis courts are featured at this smoke-free aparthotel. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 hot tubs and perks like free WiFi.

Pool

Hot Tub

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$743 nightly

$881 total

Nov 20 - Nov 21

Total with taxes and fees

A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. There's fun for all ages with a lazy river and a children's pool, and in-room childcare is an added bonus. Enjoy the 3 hot tubs and perks like free WiFi.

Pool

Hot Tub

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$266 nightly

$315 total

Nov 1 - Nov 2

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

$240 nightly

$285 total

Oct 28 - Oct 29

Total with taxes and fees

2 restaurants, 2 outdoor pools, and 3 hot tubs are among this hotel's featured amenities. 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

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$651 nightly

$772 total

Oct 30 - Oct 31

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

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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 $2,248, 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.