Title: Upcountry Maui Cottages from CA $640 | Expedia.ca [Upcountry Maui Travel Guide](https://expedia.ca/Upcountry-Maui.dx553248621593965869)[Hotels in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Hotels.d553248621593965869.Travel-Guide-Hotels)[Vacation Rentals in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Vacation-Rentals.d553248621593965869.Travel-Guide-VacationRentals)[Flights to Upcountry Maui](https://expedia.ca/Cheap-Flights-To-Upcountry-Maui.d553248621593965869.Travel-Guide-Flights)[Upcountry Maui Car Rentals](https://expedia.ca/Car-Rentals-In-Upcountry-Maui.d553248621593965869.Car-Rental-Guide)[Upcountry Maui Vacation Packages](https://expedia.ca/Upcountry-Maui.d553248621593965869.Destination-Travel-Guides) ![Haleakala Crater showing landscape views, mountains and tranquil scenes](https://images.trvl-media.com/place/501684/8ed15285-d20f-4fe9-81f0-3e0e3c2f92b8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Upcountry Maui Cottage Rentals from CA $640 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Upcountry Maui cottages ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/c3d866bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/640821ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/b81832cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/c6ff0ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath [](https://www.expedia.ca/Hana-Hotels-Beautiful-Cottage-In-The-Heart-Of-Hana.h32484007.Hotel-Information) Hana Town Center 9.6/10 Exceptional (191) "Super lovely place, I wish we were staying longer! Has everything you need. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $284 CA $640 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Hana-Hotels-Beautiful-Cottage-In-The-Heart-Of-Hana.h32484007.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/w851h563x0y1-545b8881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/w850h563x1y1-debd2996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/w850h563x1y1-9ee3eadd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/6dac1305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui [](https://www.expedia.ca/Hana-Hotels-Tropical-Romance-Lush-Gardens-In-Heavenly-Hana.h33506788.Hotel-Information) Hana 10/10 Exceptional (90) "Very unique property near Hana. Great experience!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith R. CA $427 CA $747 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Hana-Hotels-Tropical-Romance-Lush-Gardens-In-Heavenly-Hana.h33506788.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/5fd97c2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/4807a545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/2587bc99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/2e690804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded cottage on Tropical flower farm [](https://www.expedia.ca/Hana-Hotels-Secluded-Cottage-On-Tropical-Flower-Farm.h33498605.Hotel-Information) Kaʻeleku 9.4/10 Exceptional (281) "This was a great location, comfortable cute little cottage." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Briana B. CA $406 CA $767 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Hana-Hotels-Secluded-Cottage-On-Tropical-Flower-Farm.h33498605.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106210000/106203400/106203307/51afb7b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106210000/106203400/106203307/7c0970d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106210000/106203400/106203307/72291071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106210000/106203400/106203307/d5812355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy cottage nestled on our 5 acre Organic fruit farm [](https://www.expedia.ca/Hana-Hotels-Cozy-Cottage-Nestled-On-Our-5-Acre-Organic-Fruit-Farm.h106203307.Hotel-Information) Kaʻeleku 10/10 Exceptional (9) "We loved our stay! The cottage was super cute and the hosts went above and beyond by welcoming us! My favorite place we stayed and a perfect overnight for Hāna." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison W. CA $448 CA $703 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Hana-Hotels-Cozy-Cottage-Nestled-On-Our-5-Acre-Organic-Fruit-Farm.h106203307.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23290000/23288900/23288864/f09219be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/24000000/23290000/23288900/23288864/a96e2b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23290000/23288900/23288864/3f084244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/24000000/23290000/23288900/23288864/5c8e4a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops [](https://www.expedia.ca/Kihei-Hotels-Honeymoon-Cottage-Luxury.h23288864.Hotel-Information) Central Kihei 10/10 Exceptional (73) "Fantastic property that was a perfect escape and great location for exploring Maui. Would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt B. CA $544 CA $964 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Kihei-Hotels-Honeymoon-Cottage-Luxury.h23288864.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99670000/99660400/99660356/57320977.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/100000000/99670000/99660400/99660356/c53f0976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/100000000/99670000/99660400/99660356/abe22756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99670000/99660400/99660356/8bfc0bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maui bungalow - Walk to Kaanapali beach [](https://www.expedia.ca/Kaanapali-Hotels-Beach-Bungalow-W-Cruiser-Bikes-Pickleball.h99660356.Hotel-Information) Lahaina 9.2/10 Wonderful (10) "The property is very clean and we loved having the lanai available with the bbq. Definitely comes in handy with a big family who doesnt want to go out every night. We'd absolutely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin M. CA $401 CA $1,231 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Kaanapali-Hotels-Beach-Bungalow-W-Cruiser-Bikes-Pickleball.h99660356.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-29&endDate=2025-12-30®ionId=553248621593965869&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Upcountry+Maui%2C+Hawaii%2C+United+States+of+America®ionId=553248621593965869&latLong=20.754365%2C-156.241192&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Upcountry+Maui%2C+Hawaii%2C+United+States+of+America®ionId=553248621593965869&latLong=20.754365%2C-156.241192&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Upcountry+Maui%2C+Hawaii%2C+United+States+of+America®ionId=553248621593965869&latLong=20.754365%2C-156.241192&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Upcountry+Maui%2C+Hawaii%2C+United+States+of+America®ionId=553248621593965869&latLong=20.754365%2C-156.241192&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Upcountry+Maui%2C+Hawaii%2C+United+States+of+America®ionId=553248621593965869&latLong=20.754365%2C-156.241192&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Upcountry+Maui%2C+Hawaii%2C+United+States+of+America®ionId=553248621593965869&latLong=20.754365%2C-156.241192&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=VACATION_HOME) Villas [](https://www.expedia.ca/Hotel-Search?destination=Upcountry+Maui%2C+Hawaii%2C+United+States+of+America®ionId=553248621593965869&latLong=20.754365%2C-156.241192&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=VILLA) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FUpcountry-Maui-Cottages.d553248621593965869-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpcountry-Maui-Cottages.d553248621593965869-aaCottages.Travel-Guide-Accommodation) ## Top Upcountry Maui Hotel Reviews ![Maui Beach Hotel](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/d9caacb9_y.jpg) ### Maui Beach Hotel 10/10 Excellent "Awesome staff awesome view couldn’t ask for more from this quaint cute hotel vibe!" [](https://expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information) ![The Westin Maui Resort & Spa, Ka'anapali](https://images.trvl-media.com/lodging/1000000/30000/25900/25837/87f76342_y.jpg) ### The Westin Maui Resort & Spa, Ka'anapali 10/10 Excellent "Great location, friendly staff, good amenities including restaurants amd pools. Hospitality room on last day was clean and available when needed." [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information) ![OUTRIGGER Kaanapali Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/11600/11554/82021c2d_y.jpg) ### OUTRIGGER Kaanapali Beach Resort 10/10 Excellent "We had a wonderful stay at the resort. Staff was very accommodating and friendly, room was very clean and didn't have a musty smell like a lot of hotels do, and best of all, it was right in the middle of all the stuff to do in the area. I highly recommend staying there!" [](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information) ![Wailea Beach Resort - Marriott, Maui](https://images.trvl-media.com/lodging/1000000/30000/20400/20303/b323b293_y.jpg) ### Wailea Beach Resort - Marriott, Maui 10/10 Excellent "It was a great place to stay with my family for my 4-year-old twin's birthday, and there were a lot of activities to do such as yoga, pilates, kids activities, and among all other things. Not to mention the road trip that we’ve taken to Hana, which was very nice and fun." [](https://expedia.ca/Kihei-Hotels-Wailea-Beach-Resort-Marriott.h20303.Hotel-Information) ![Maui Coast Hotel](https://images.trvl-media.com/lodging/1000000/30000/28700/28645/ffbd6b5d_y.jpg) ### Maui Coast Hotel 10/10 Excellent "Honestly, one of the best hotel stays I’ve ever had! The amenities and service for the price point were outstanding. Every service member we encountered was helpful, kind, enthusiastic, and helpful. The staff was always very accommodating, the room was clean and spacious, and the view from the pool was great. Wonderful location, both in Kihei and also on the island as you have easy access to the north, east or west of the island. The hotel is directly across the street from the beach and has two grocery stores within walking distance. I would 100% recommend this hotel and will definitely stay again if I return." [](https://expedia.ca/Kihei-Hotels-Maui-Coast-Hotel.h28645.Hotel-Information) ![Maui Seaside Hotel](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/b53bdaab_y.jpg) ### Maui Seaside Hotel 10/10 Excellent "The staff was very friendly and always ready to check your needs." [](https://expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information) ![Fairmont Kea Lani Maui](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg) ### Fairmont Kea Lani Maui 10/10 Excellent "Friendly staff, good restaurant" [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![Royal Lahaina Resort & Bungalows](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/8a8031c5_y.jpg) ### Royal Lahaina Resort & Bungalows 10/10 Excellent "Clean room, friendly staff, amenities were great. We loved the bars & the beauty of the property " [](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) ![OUTRIGGER Honua Kai Resort & Spa](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/cc604c30_y.jpg) ### OUTRIGGER Honua Kai Resort & Spa 10/10 Excellent "Amazing staff so friendly. Very clean. Definitely going back and staying there again." [](https://expedia.ca/Lahaina-Hotels-Honua-Kai-Resort-Spa.h2740153.Hotel-Information) ## Find out more about Upcountry Maui ## Upcountry Maui Cottages information | Number of reviews | 617 | | ----------------- | ----------- | | Accommodation | 27 Cottages | | Lowest Price | CA $640 | | Highest Price | CA $1,231 | ## Frequently asked questions ### How much do cottages in Upcountry Maui cost? ### How many cottages are there in Upcountry Maui? ### Why book your cottage in Upcountry Maui with Expedia? ### How can I find cheap cottages in Upcountry Maui? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Maui ](https://www.expedia.ca/5Star-Maui-Hotels.s50-0-d180073.Travel-Guide-Filter-Hotels) - [Hotels near Haleakala Crater ](https://www.expedia.ca/Haleakala-Crater-Hotels.0-l501684-0.Travel-Guide-Filter-Hotels) - [Hotels near Haleakala National Park ](https://www.expedia.ca/Haleakala-National-Park-Hotels.0-l507525-0.Travel-Guide-Filter-Hotels) - 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