Upcountry Maui Vacation Packages 2026 from $1,227

Upcountry Maui flight + hotel vacation packages

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

Maui Banyan Vacation Club

South Kihei

$1,227

per person

Nov 18 - Nov 24

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.

Hotel Wailea Maui

Wailea

$3,970

per person

Dec 20 - Dec 26

found 16 hours 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 laundry service, conference center, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free beach shuttle.

Maui Beach Vacation Club

North Kihei

$1,645

per person

Nov 18 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Fairmont Kea Lani Maui

Wailea

Save 100% on your flight

$3,801

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Kahului (OGG)

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.

Kamaole Sands - Maui Condo & Home

South Kihei

Save 100% on your flight

$2,142

per person

Dec 20 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Phoenix (PHX) to Kahului (OGG)

4 outdoor tennis courts, an outdoor pool, and a hot tub are all featured at this smoke-free condo. There's a picnic area and multilingual staff can provide around-the-clock assistance.

Top Upcountry Maui hotels deals

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

$185 nightly

$220 total

Sep 29 - Sep 30

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

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$860 nightly

$1,021 total

Oct 12 - Oct 13

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.

Maui Coast Hotel

2259 S Kihei Rd Kihei HI

Free Cancellation

Reserve now, pay when you stay

$257 nightly

$305 total

Sep 29 - Sep 30

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

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$518 nightly

$614 total

Oct 26 - Oct 27

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.

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$248 nightly

$295 total

Sep 29 - Sep 30

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.

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$468 nightly

$555 total

Oct 27 - Oct 28

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.

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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 $1,227, 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.