Deals on vacations and trips to Upcountry Maui

Save when you book Upcountry Maui package deals

Search stays

Upcountry Maui flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
Save 100% on your flight
per person
Aug 5 - Aug 12
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
This aparthotel features a full-service spa, 2 outdoor pools, and a restaurant. Enjoy the 24-hour gym and perks like free self parking. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3 out of 5
Save 100% on your flight
per person
Aug 5 - Aug 12
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
Aug 8 - Aug 13
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
This aparthotel features an outdoor pool and an outdoor tennis court. Enjoy the spa tub and perks like free self parking and free WiFi. A garden, dry cleaning, and concierge services are also on offer.
Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

3.5 out of 5
Save 100% on your flight
per person
Aug 5 - Aug 12
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
An outdoor pool, free self parking, and concierge services are featured at this aparthotel. A terrace, a garden, and a picnic area are also on offer.
Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach

4 out of 5
Save 100% on your flight
per person
Aug 5 - Aug 12
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
This condo features an outdoor pool and a gym. Enjoy the outdoor tennis court and perks like free self parking. There's a spa tub on site, and a 24-hour front desk and a garden are also provided.

Top Upcountry Maui hotel deals

Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd, Kihei, HI
Free Cancellation
Reserve now, pay when you stay
The price is $227 per night
$227
per night
Jun 9 - Jun 10
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle. You'll appreciate the outdoor tennis court, poolside bar, and laundry facilities.
Hot Tub
Breakfast available
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy, Lahaina, HI
Free Cancellation
Reserve now, pay when you stay
The price is $274 per night
$274
per night
Jun 12 - Jun 13
A full-service spa, 2 outdoor pools, and a restaurant are all featured at this aparthotel. There's fun for all ages with a children's pool and an arcade/game room, and barbecue grills are available on site. Enjoy the gym and unwind at the bar/lounge and poolside bar.
Hot Tub
Pool
Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui

4 out of 5
104 Kaanapali Shores Pl, Lahaina, HI
The price is $247 per night
$247
per night
Jul 1 - Jul 2
This hotel features a restaurant, an outdoor pool, and a bar/lounge. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Business travelers can take advantage of the business center.
Breakfast available
Pool
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
The price is $824 per night
$824
per night
Jun 7 - Jun 8
A full-service spa, 5 restaurants, and 9 outdoor pools are all featured at this resort. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. 2 poolside bars and 2 bars/lounges are featured at this resort, along with a gym.
Hot Tub
Breakfast available
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4 out of 5
2365 Kaanapali Pkwy, Lahaina, HI
Free Cancellation
Reserve now, pay when you stay
The price is $759 per night
$759
per night
Jun 2 - Jun 3
A full-service spa, 2 restaurants, and 3 outdoor pools are all featured at this smoke-free 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.
Pet friendly
Pool
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

4 out of 5
200 Nohea Kai Dr, Lahaina, HI
Free Cancellation
Reserve now, pay when you stay
The price is $557 per night
$557
per night
Jun 12 - Jun 13
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.
Hot Tub
Breakfast available
Don't see what you're looking for?
See all available properties in Upcountry Maui
View all properties
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

Image for Wailea Beach

Wailea Beach

4.5/5(1,614 reviews)

This stretch of powdery sand is part of an upscale resort community and is an ideal place to sunbathe, snorkel, and dive with Hawaiian green turtles and manta rays.

Wailea Beach
Image for Haleakala National Park

Haleakala National Park

4.5/5(697 reviews)

From mountain peaks to forested valleys, from the Pacific coastline to a volcanic crater, this national park encompasses a great diversity of natural habitats.

Haleakala National Park
Image for Maui Ocean Center

Maui Ocean Center

4.5/5(964 reviews)

Make time to visit the sea animals who live in Maui Ocean Center during your trip to Maalaea. Wander the area's seaside or simply enjoy one of its seafood restaurants.

Maui Ocean Center

Photos of local treasures

Maui Island featuring landscape views

Frequently asked questions

How much are vacation packages to Upcountry Maui?
You can pick up a great flight and hotel bundle for an affordable $1,395. With one of our Travelocity vacation packages, an escape to Upcountry Maui has never been more tempting! Save your time and money and get an early start with packing your suitcases.
Where can I get the best vacation package deals for Upcountry Maui?
It’s hard to top Travelocity when it comes to finding your Upcountry Maui package deal. There are at least 400 partner airlines and 1,000,000 worldwide properties to select from. Book your trip now and get ready to tick another exciting destination off your must-visit list.
Why should I purchase my Upcountry Maui vacation package via Travelocity?
From incredible destinations to memorable experiences, we have everything you need to appease your wanderlust. Our 24/7 support will also ensure you’re taken care of while you’re on your vacation. And don’t panic if you find a lower price on your booking, we’ll match it. That’s our Price Match Guarantee.
Can I save on my Upcountry Maui car rental if I book it with my hotel or flight?
Combining your bookings into an Upcountry Maui vacation package will save you a handsome sum. Choose a car and flight; a hotel, flight and car; or a car and hotel. You won’t find a better way to explore the greater Upcountry Maui region than from behind the wheel of your own rental car. You can also add tours and experiences to your Travelocity package.
What is the best time of year to go to Upcountry Maui?
If you want to avoid expensive flights, tourist crowds and booked-out hotels, organize your trip outside of March, July and November. The quietest time to travel around Upcountry Maui is January, April and December. You’ll find the highest hotel rates in and the most affordable in .
Which airport is best for Upcountry Maui?
Kahului Airport (OGG) is one of the most popular airports for people jetting into Upcountry Maui. Molokai Airport (MKK) and Lanai Airport (LNY) also welcome numerous flights to the region.