Upcountry Maui Vacation Packages
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Top Upcountry Maui vacation package deals
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Maui Beach Vacation Club
North Kihei
8.4/10 Very Good! (937 reviews)
Nov 1 - Nov 7
6 night stay
Dallas (DFW) to Kahului (OGG)
American Airlines • Coach
Kahului (OGG) to Dallas (DFW)
Alaska Airlines • Coach
Price was $1,646, price is now $1,162 per person
$1,162
per person
found 1 day ago
Frustrated that I paid for an OCEAN VIEW ROOM (paid more for this room!!) but was not given that and was told that “that is only as available”. This should not be marketed this way. If you pay more for a specific amenity you should get what you pay for. I would NOT have stayed here if I knew I wouldn’t get an ocean view room.
The place was nice in the end but the this was frustrating.
Reviewed on Sep 20, 2026
5.0-star property
Fairmont Kea Lani Maui
Wailea
9.6/10 Exceptional! (1,003 reviews)
Oct 23 - Oct 29
6 night stay
Dallas (DFW) to Kahului (OGG)
Southwest Airlines • Non-stop • Coach
Kahului (OGG) to Dallas (DFW)
Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $4,685, price is now $2,960 per person
$2,960
per person
found 1 day ago
3.5-star property
Palms at Wailea Maui
Wailea
8.4/10 Very Good! (547 reviews)
Dec 10 - Dec 17
7 night stay
Portland (PDX) to Kahului (OGG)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,627, price is now $1,870 per person
$1,870
per person
found 1 day ago
Great stay!
Reviewed on Sep 19, 2026
3.0-star property
Castle Kama'ole Sands
South Kihei
8/10 Very Good! (2,346 reviews)
Dec 1 - Dec 9
8 night stay
Los Angeles (LAX) to Kahului (OGG)
Alaska Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,784, price is now $1,281 per person
$1,281
per person
found 17 hours ago
We had everything we needed.
Reviewed on Sep 1, 2026
Top rated hotels for your Upcountry Maui vacation package
Gods Peace Of Maui
1290 Haliimaile Rd Makawao HI
9.9 mi from city center
$185 nightly
The price is $220 total per night
$220 total
Sep 23 - Sep 24
Total with taxes and fees
Gods Peace Of Maui features free WiFi in public areas, microwave in a common area, and refrigerator in a common area. There's free parking if you drive. Additional amenities include a library, barbecue grills, and a garden.
Breakfast included
Pet friendly
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
Free Cancellation
Reserve now, pay when you stay
13.4 mi from city center
$269 nightly
The price is $319 total per night
$319 total
Sep 27 - Sep 28
Total with taxes and fees
At Maui Coast Hotel, guests enjoy 2 outdoor pools, a children's pool, and a 24-hour gym. Parking is available for USD 20.94 per night (USD 26.18 per night for valet parking), and there's also a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry and securing valuables. Additional amenities include 3 hot tubs, free WiFi in public areas, and free use of bicycles.
Pool
Hot Tub
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
13.71 mi from city center
$860 nightly
The price is $1,021 total per night
$1,021 total
Oct 9 - Oct 10
Total with taxes and fees
Guests of Grand Wailea Maui, A Waldorf Astoria Resort have access to a full-service spa, 9 outdoor pools, and a lazy river. Valet parking is offered for USD 80 per night. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, securing valuables, and dry cleaning/laundry. Other amenities at this luxury resort include a children's pool, a 24-hour gym, and 3 hot tubs.
Pool
Hot Tub
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.
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