
Upcountry Maui Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Photo by Project Forever
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 1 day 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

Maui Beach Vacation Club
North Kihei
Price was CA $3,795, price is now CA $2,804 per person
CA $2,804
per person
Sep 9 - Sep 16
found 4 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8.4/10 Very good! (903 reviews)
No air conditioning- hot tub was down 3 of 6 days
Reviewed on Jul 8, 2026

The Residences at Kamaole Sands Resort
South Kihei
Price was CA $2,180, price is now CA $1,678 per person
CA $1,678
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
10/10 Exceptional! (2 reviews)
The place was very clean. The staff was very communicative and accommodating. I stayed Wednesday-Sunday and I extended my stay 1 night which was very fast and easy. They left us chairs and towels which was very nice for the beach. The place was very spacious for 2 people. If you want to cook this has plenty of counter space. The balcony had a partial ocean view which was very nice. Great value for your money. Check in/out was very easy. You can walk right to the best beaches around.
Only Cons I can think of: Not a lot of blankets and the wifi in the bedroom didn’t really work, it was low signal. It would’ve been nice to watch Netflix from the bedroom. That’s the only negative I can think of.
Reviewed on Feb 24, 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 1 day 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
Upcountry Maui Hotel Deals

Gods Peace Of Maui
1290 Haliimaile Rd Makawao HI
The price is CA $236 per night from Jul 23 to Jul 24
CA $236
CA $280 total
Jul 23 - Jul 24
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 $1,148 per night from Aug 9 to Aug 10
CA $1,148
CA $1,454 total
Aug 9 - Aug 10
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 $1,019 per night from Jul 19 to Jul 20
CA $1,019
CA $1,291 total
Jul 19 - Jul 20
includes taxes & fees
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
Frequently asked questions
Explore a world of travel with Expedia
- Kaanapali Hotels
- Wailea Hotels
- Hilton Hotels in Maui
- B&B in Upcountry Maui
- Villas in Maui
- Beach Hotel Hotels in Maui
- Best Western Hotels in Maui
- Romantic Hotels in Maui
- B&B in Maui
- Hotels near Haleakala Crater
- All Inclusive Resorts and in Maui
- Boutique Hotels in Maui
- 5 Star Hotels in Maui
- Wyndham Hotels in Maui
- Kihei Hotels
- Family Hotels in Maui
- Oceanfront Hotels in Maui
- Apartments in Maui
- Adults Only Resorts & in Maui
- Kahului Hotels
- Hotels with Kitchenettes in Maui
- 5 Star Hotels in Upcountry Maui
- Hotels with Free Airport Shuttle in Maui
- Hotels with Waterslides in Maui
- Condo Rentals in Maui
- Cheap Hotels in Maui
- Hilton Grand Vacations Club Maui Bay Villas
- Hotels near Haleakala National Park
- Vacation Homes in Upcountry Maui
- Condo Rentals in Kihei
- Cottages in Maui
- Hotels near Kahului
- Hostels in Maui
- Honeymoon Resorts and in Maui
- Exceptional Ocean Views
- Hana Hotels
- 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)
- Flights from Vancouver (YVR) to Kahului (OGG)
- Flights from Victoria (YYJ) to Kahului (OGG)
- 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.








