Upcountry Maui Vacation Packages 2025/2026 from $999

Upcountry Maui flight + hotel vacation packages

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

Royal Lahaina Resort & Bungalows

Save 100% on your flight

$999

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

A full-service spa, 2 outdoor pools, and 11 outdoor tennis courts are featured at this eco-certified hotel. 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.

Hyatt Vacation Club at Ka'anapali Beach, Maui

Save 100% on your flight

$1,979

per person

Nov 30 - Dec 5

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Kahului (OGG)

This eco-certified hotel features 2 outdoor pools, a bar/lounge, and a poolside bar. Enjoy the 24-hour gym and perks like free WiFi. Valet parking, a coffee shop, and a garden are also offered.

Kahana Beach Vacation Club

$1,093

per person

Dec 4 - Dec 10

found 22 hours ago

Roundtrip 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.

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

Save 100% on your flight

$2,646

per person

Dec 19 - Dec 24

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

This luxury resort includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Unwind with a drink at the poolside bar and enjoy perks like a free beach shuttle.

Royal Lahaina Bungalows & Spa

Save 100% on your flight

$1,304

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

A full-service spa, 2 outdoor pools, and 11 outdoor tennis courts are all featured at this luxury aparthotel. 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.

Top Upcountry Maui hotels deals

Gods Peace Of Maui

1290 Haliimaile Rd, Makawao, HI

$185 nightly

$218 total

Sep 30 - Oct 1

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

Aston Maui Kaanapali Villas

45 Kai Ala Dr, Lahaina, HI

Free Cancellation

Reserve now, pay when you stay

$316 nightly

$373 total

Oct 6 - Oct 7

Total with taxes and fees

This aparthotel features a full-service spa, 2 outdoor pools, and 2 hot tubs. There's a restaurant and a bar/lounge for dining and drinks, and also a 24-hour gym on site.

Pool

Hot Tub

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr, Lahaina, HI

Free Cancellation

Reserve now, pay when you stay

$259 nightly

$305 total

Oct 29 - Oct 30

Total with taxes and fees

Pool

Spa

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy, Lahaina, HI

Free Cancellation

Reserve now, pay when you stay

$288 nightly

$340 total

Oct 28 - Oct 29

Total with taxes and fees

This aparthotel's full-service spa, 2 outdoor pools, and 2 outdoor tennis courts are some of the highlights. Enjoy the 2 hot tubs and gym, and unwind with a drink at the bar/lounge.

Pool

Hot Tub

Maui Coast Hotel

2259 S Kihei Rd, Kihei, HI

Free Cancellation

Reserve now, pay when you stay

$249 nightly

$293 total

Oct 21 - Oct 22

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

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy, Lahaina, HI

Free Cancellation

Reserve now, pay when you stay

$536 nightly

$632 total

Oct 15 - Oct 16

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.

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.

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.

Leleiwi Overlook

Explore the great outdoors at Leleiwi Overlook, a lovely green space in Kula. Amble around this relaxing area's seaside, or seek out the yoga studios.

Frequently asked questions

How much are vacation packages to Upcountry Maui?

With deals starting at just $999, 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.