Upcountry Maui Vacation Packages 2026 from $1,062

Name: Aston Kaanapali Shores
Price range: $242 total

Upcountry Maui flight + hotel vacation packages

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

Aston Maui Hill

South Kihei

$1,062

per person

Nov 16 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

This aparthotel features an outdoor pool and an outdoor tennis court. Enjoy the hot tub and perks like free self parking and free WiFi. A garden, dry cleaning, and concierge services are also on offer.

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

Save 100% on your flight

$1,960

per person

Nov 16 - Nov 20

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 laundry service, conference center, and valet parking. A free beach shuttle is offered as well.

Maui Beach Vacation Club

North Kihei

$1,555

per person

Nov 1 - Nov 6

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

The Kalama Residence

South Kihei

Save 100% on your flight

$4,991

per person

Nov 18 - Nov 24

found 10 hours ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

An outdoor pool, free self parking, and laundry facilities are featured at this apartment. A terrace and a virtual front desk are also provided.

Signature Residences at Maui Banyan

South Kihei

Save 100% on your flight

$1,382

per person

Nov 18 - Nov 24

found 10 hours ago

Roundtrip non-stop flight included

Denver (DEN) to Kahului (OGG)

This condo's 2 outdoor pools and outdoor tennis court are among the featured amenities. Enjoy the hot tub and perks like free self parking. A terrace, barbecue grills, and a virtual front desk are also on offer.

Top Upcountry Maui hotels deals

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

$213 nightly

$253 total

Sep 17 - Sep 18

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

Maui Coast Hotel

2259 S Kihei Rd Kihei HI

Free Cancellation

Reserve now, pay when you stay

$231 nightly

$274 total

Sep 27 - Sep 28

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

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$504 nightly

$599 total

Sep 12 - Sep 13

Total with taxes and fees

This resort features a golf course, a full-service spa, and 4 restaurants. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the 6 outdoor pools and gym, and unwind with a drink at the poolside bar.

Pool

Hot Tub

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy Lahaina HI

Free Cancellation

Reserve now, pay when you stay

$204 nightly

$242 total

Sep 23 - Sep 24

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

The Ritz-Carlton Maui, Kapalua

1 Ritz-Carlton Drive Kapalua HI

$858 nightly

$1,019 total

Sep 11 - Sep 12

Total with taxes and fees

This luxury resort features a golf course, a full-service spa, and 6 restaurants. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. Enjoy the 3 outdoor pools and perks like a free beach shuttle.

Pool

Hot Tub

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$786 nightly

$933 total

Sep 23 - Sep 24

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

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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 $1,062, 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.