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.
Castle at Maui Banyan

Castle at Maui Banyan

3.5 out of 5
South Kihei
Price was $1,759, price is now $749 per person
$749
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
This hotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden and barbecue grills are also provided.
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was $1,492, price is now $844 per person
$844
per person
Jan 26 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Wailea
Save 100% on your flight
Price was $4,062, price is now $2,303 per person
$2,303
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
This luxury resort includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free beach shuttle.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was $2,577, price is now $1,594 per person
$1,594
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Grand Champions

Grand Champions

2.5 out of 5
Wailea
Price was $2,615, price is now $1,726 per person
$1,726
per person
Feb 3 - Feb 9
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Kahului (OGG)
This resort features an outdoor pool and a hot tub. Free self parking, a terrace, and a garden are also offered.

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
Nov 14 - Nov 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
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
$206 nightly
The price is $245 total per night
$245 total
Nov 15 - Nov 16
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
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
2780 Kekaa Dr Lahaina HI
Free Cancellation
Reserve now, pay when you stay
$248 nightly
The price is $294 total per night
$294 total
Nov 18 - Nov 19
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.
Pool
Spa
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$742 nightly
The price is $881 total per night
$881 total
Dec 11 - Dec 12
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
$633 nightly
The price is $751 total per night
$751 total
Nov 28 - Nov 29
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
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
$288 nightly
The price is $342 total per night
$342 total
Nov 24 - Nov 25
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
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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 $749, 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 rugged mountain landscape with rocky outcrops and a valley.
A mountainous landscape with distinct red and brown hues, a prominent peak, and clouds at the mountain base.
A rugged mountain landscape with a valley and distant peaks under a clear sky.
A volcanic landscape with rugged mountains and a clear sky.

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