
Upcountry Maui Vacation Packages
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Top Upcountry Maui Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Deluxe Oceanside Resort Vistas
Central Kihei
Price was CA $1,968, price is now CA $1,530 per person
CA $1,530
per person
Sep 8 - Sep 13
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
9.6/10 Exceptional! (4 reviews)
It is a nice 1 bedroom suite with sleeping for 5 including a sofa bed. They have all the amenities available including beach chairs, towels, beach umbrellas. Also the kitchen is full stocked with pots and table ware along with coffee and other condiments. The AC was great, and so was the internet and cable ready. We used our own accts for netflix and prime. Cleaning supplies were also plentiful along with a vacum. They also had an ironing board laundry detergent, hair dryer and plenty of toiletries. They had some board games to keep the kids entertained. The balcony had a neat ocean view with nice patio furniture. It is in a very convienient location wuth a nice ocean view and plenty of parking. The kids borrowed some golf clubs for some 4 hole course. The bbq facilities were also great and clean. We will definitely come back for another stay. Also the neigborhood is pretty safe.
Reviewed on Jun 16, 2026

Grand Champions
Wailea
Price was CA $3,076, price is now CA $2,394 per person
CA $2,394
per person
Sep 13 - Sep 20
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
9.2/10 Wonderful! (5 reviews)
Grand Champions exceeded every expectation. The property is beautifully maintained with lush tropical landscaping that instantly sets the tone for a relaxing Maui getaway. The unit was spotless, well-appointed, and had everything we needed — the kitchen was fully equipped, the beds were comfortable, and the lanai was the perfect spot for morning coffee.
The location in Wailea is unbeatable: quiet and private, yet minutes from world-class beaches, restaurants, and Shops at Wailea. The pools were pristine and never crowded, and the grounds feel more like a resort than a condo complex.
Check-in was seamless and communication with the host was prompt and professional throughout. We’d absolutely stay here again and recommend it to anyone looking for a comfortable, upscale base to explore South Maui. Mahalo!
Reviewed on Apr 20, 2026


Grand Wailea Maui, A Waldorf Astoria Resort
Wailea
Price was CA $4,084, price is now CA $3,220 per person
CA $3,220
per person
Sep 19 - Sep 24
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
8.8/10 Excellent! (1,004 reviews)
The prices to everything there is disrespectful straight up!
Reviewed on Jul 8, 2026

Maui Beach Vacation Club
North Kihei
Price was CA $2,867, price is now CA $2,277 per person
CA $2,277
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
8.4/10 Very good! (903 reviews)
If you arrive late Mark the night security is very helpful. If you need a travel consultants concierge Cecilia is awesome
The whole staff is amazing. Thank you very much for everything not ready yet
Reviewed on Jul 5, 2026
Upcountry Maui Hotel Deals

Gods Peace Of Maui
1290 Haliimaile Rd Makawao HI
The price is CA $236 per night from Jul 21 to Jul 22
CA $236
CA $281 total
Jul 21 - Jul 22
includes taxes & fees
8.8/10 Excellent! (126 reviews)
"Our stay at Cottage Peace of Maui was absolutely wonderful! The cottage was clean, comfortable, peaceful, and had everything our family needed for a relaxing vacation. The location was perfect for exploring the island while still enjoying a quiet retreat. A very special thank you to Mika and Tammi ..."
Reviewed on Jun 26, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
The price is CA $1,167 per night from Jul 21 to Jul 22
CA $1,167
CA $1,478 total
Jul 21 - Jul 22
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"The prices to everything there is disrespectful straight up!"
Reviewed on Jul 8, 2026

The Westin Maui Resort & Spa, Ka'anapali
2365 Kaanapali Pkwy Lahaina HI
Fully refundableReserve now, pay when you stay
The price is CA $1,021 per night from Jul 19 to Jul 20
CA $1,021
CA $1,294 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (1,107 reviews)
"Amazing staff, tons for families to do, not just pool, whalers shopping, and the lanai!"
Reviewed on Jul 8, 2026
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
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- Exceptional Ocean Views
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- Flights to Maui
- Flights from Los Angeles (LAX) to Kahului (OGG)
- Flights from Maui
- Flights from Honolulu (HNL) to Kahului (OGG)
- Flights from Edmonton (YEG) to Kahului (OGG)
- Flights from Toronto (YYZ) to Kahului (OGG)
- Flights from Calgary (YYC) to Kahului (OGG)
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- Flights from Kahului
- Haleakala Crater
- Waipuilani Park
- All inclusive Vacation Packages Maui
- Kahului Vacations
- Maui Nui Botanical Gardens
- Kamaole Beach Park 3
- Wailea Blue Golf Course
- Wailea Beach
- Ahihi Kinau Natural Area Reserve
- Visit Maui
- Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters
- Molokini
- Haleakala National Park
- Keawakapu Beach North
- Hana Vacations
- Hamoa Beach
- Makena State Park Beach
- Kokomo Vacations
- Koki Beach Park
- Hoʻokipa Beach Park
- Kihei Vacations
- Visit Upcountry Maui
- Paia Vacations
- Kuau Bay Beach
- Kamaole Beach Park 2
- Makena Vacations
- Garden of Eden Arboretum
- Iao Valley State Park
- Maluaka Beach
- Wailea Vacations
- Oneuli Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







