Deals on vacations and trips to Upcountry Maui

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Upcountry Maui flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Save 100% on your flight
Price was $1,574, price is now $1,010 per person
$1,010
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Portland (PDX) 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, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Save 100% on your flight
Price was $7,025, price is now $4,241 per person
$4,241
per person
Nov 1 - Nov 7
found 24 hours ago
Roundtrip non-stop flight included
Portland (PDX) 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

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was $1,612, price is now $1,194 per person
$1,194
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.
Grand Champions

Grand Champions

2.5 out of 5
Wailea
Price was $1,533, price is now $1,158 per person
$1,158
per person
Nov 17 - Nov 21
found 22 hours ago
Roundtrip flight included
San Francisco (SFO) to Kahului (OGG)
This resort features an outdoor pool and a hot tub. Free self parking, a terrace, and a garden are also offered.
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Wailea
Save 100% on your flight
Price was $2,573, price is now $1,948 per person
$1,948
per person
Oct 13 - Oct 20
found 3 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Kahului (OGG)
This aparthotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Top Upcountry Maui hotels deals

Gods Peace Of Maui

Gods Peace Of Maui

2 out of 5
1290 Haliimaile Rd Makawao HI
$185 nightly
The price is $220 total per night
$220 total
Sep 14 - Sep 15
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

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd Kihei HI
Free Cancellation
Reserve now, pay when you stay
$251 nightly
The price is $298 total per night
$298 total
Sep 28 - Sep 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
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

4 out of 5
200 Nohea Kai Dr Lahaina HI
$504 nightly
The price is $599 total per night
$599 total
Sep 16 - Sep 17
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
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$786 nightly
The price is $933 total per night
$933 total
Oct 1 - Oct 2
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
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

5 out of 5
2365 Kaanapali Pkwy Lahaina HI
Free Cancellation
Reserve now, pay when you stay
$660 nightly
The price is $783 total per night
$783 total
Oct 4 - Oct 5
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
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
1 Ritz-Carlton Drive Kapalua HI
$858 nightly
The price is $1,019 total per night
$1,019 total
Sep 18 - Sep 19
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
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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 $1,010, 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.

Photos of local treasures

Browse Upcountry Maui vacation photos for more inspiration

A barren volcanic landscape with rugged terrain and distant mountains.
A person walking on a wooden bridge surrounded by bamboo trees.
A barren landscape with a clear sky, a distant mountain range, and a few people walking on a path.
A vast volcanic landscape with distinct ridges and valleys.
A narrow wooden path through a dense forest with tall trees and lush green foliage.

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