Title: Upcountry Maui Cottages | 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) ![](https://mediaim.expedia.com/destination/9/01b28fa5aec642d0f16d83dbe59a5809.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Upcountry Maui Cottage Rentals ![](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 Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Upcountry Maui Cottages ![Exterior](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/7c06baf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/eeb50dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/be9ac5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/9c5769aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath Hana 9.6/10 Exceptional (189) "Super lovely place, I wish we were staying longer! Has everything you need. " CA $289 CA $650 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Hana-Hotels-Beautiful-Cottage-In-The-Heart-Of-Hana.h32484007.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27270000/27263900/27263838/f708db35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27270000/27263900/27263838/2ffa056c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/28000000/27270000/27263900/27263838/0db66bb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27270000/27263900/27263838/w3235h2400x0y25-e0fffc0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Great location between Hana Town and Hamoa Beach, private, family-friendly Hana 9.8/10 Exceptional (232) "Good location & great experience" CA $371 CA $712 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Hana-Hotels-Great-Location-Between-Hana-Town-And-Hamoa-Beach.h27263838.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) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/0a266b6d.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) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/9bf9b442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui Hana 10/10 Exceptional (87) "After eight trips to Hawaii, this is the first place where I really felt I was in paradise. " CA $434 CA $760 total includes taxes & fees Oct 26 - Oct 27 [](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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/0e7693c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/6a813fc7.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 Hana 9.4/10 Exceptional (272) "The cottage was great. Check-in was stress-free and Ms. Rebecca was always responsive. " CA $413 CA $778 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Hana-Hotels-Secluded-Cottage-On-Tropical-Flower-Farm.h33498605.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) ![Interior](https://images.trvl-media.com/lodging/24000000/23290000/23288900/23288864/52aa9d54.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) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23290000/23288900/23288864/37118a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops Central Kihei 10/10 Exceptional (72) "This charming cottage is a marvel of great design, surrounded by a beautiful garden. We enjoyed walking through the friendly neighborhood on our way to town. The owners are skilled, organized inn keepers. All contributed to a wonderful week on Maui." CA $420 CA $797 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Kihei-Hotels-Honeymoon-Cottage-Luxury.h23288864.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99670000/99660400/99660356/a3fdbaa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/100000000/99670000/99660400/99660356/cb2c9be9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/100000000/99670000/99660400/99660356/w1286h711x2y0-48483f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99670000/99660400/99660356/a6d6347f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bungalow walk to beach + Pickleball gear and Bikes Lahaina 9.2/10 Wonderful (10) "We often had the pool to ourselves, occasionally sharing it with at most one other family. The location is convenient and it was easy to get to many different beaches. One thing to be aware of: the loft ceiling is quite low and the space there is tight. The extra twin rollout bed is at the floor level. " CA $387 CA $1,224 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Kaanapali-Hotels-3-Bed-2-Bath-Beach-Bungalow-W-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=2025-10-26&endDate=2025-10-27®ionId=553248621593965869&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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 ![Aston Kaanapali Shores](//images.trvl-media.com/lodging/1000000/10000/1300/1284/cb6fb615_y.jpg) ### Aston Kaanapali Shores 10/10 Excellent "The staff were very helpful and were able to accommodate us for an early check in. We were very pleased with our room, and the grounds around the hotel are beautiful. I loved that it was right on the beach which ended up being a pretty good beach for us. We even saw 3 turtles while snorkeling there! The only thing we weren’t prepared for was how noisy the Myna birds were! They were squawking even in the middle of the night!" [](https://expedia.ca/Lahaina-Hotels-Aston-Kaanapali-Shores.h1284.Hotel-Information) ![Hyatt Regency Maui Resort & Spa](//images.trvl-media.com/lodging/1000000/20000/19300/19207/3102d1ec_y.jpg) ### Hyatt Regency Maui Resort & Spa 10/10 Excellent "Nice staff, rooms were clean and I like the option to opt out of housecleaning for a refund. " [](https://expedia.ca/Lahaina-Hotels-Hyatt-Regency-Maui.h19207.Hotel-Information) ![The Westin Maui Resort & Spa, Ka'anapali](//images.trvl-media.com/lodging/1000000/30000/25900/25837/87f76342_y.jpg) ### The Westin Maui Resort & Spa, Ka'anapali 10/10 Excellent "Room and view were great. Staff was EXCELLENT. Pool outstanding." [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information) ![Grand Wailea Maui, A Waldorf Astoria Resort](//images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997_y.jpg) ### Grand Wailea Maui, A Waldorf Astoria Resort 10/10 Excellent "The property is beautiful " [](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ![Royal Lahaina Resort & Bungalows](//images.trvl-media.com/lodging/1000000/40000/34800/34767/8a8031c5_y.jpg) ### Royal Lahaina Resort & Bungalows 10/10 Excellent "Yes. Higher floor would have been better but still the view was amazing." [](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) ![OUTRIGGER Kaanapali Beach Resort](//images.trvl-media.com/lodging/1000000/20000/11600/11554/82021c2d_y.jpg) ### OUTRIGGER Kaanapali Beach Resort 10/10 Excellent "excellent" [](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information) ![Aston Maui Kaanapali Villas](//images.trvl-media.com/lodging/1000000/20000/18800/18735/6389d34f_y.jpg) ### Aston Maui Kaanapali Villas 10/10 Excellent "Early check ins are not an option. The staff sent mixed messages about checking in. Not pleased, the resort was really nice. " [](https://expedia.ca/Lahaina-Hotels-Aston-Maui-Kaanapali-Villas.h18735.Hotel-Information) ![Sheraton Maui Resort & Spa](//images.trvl-media.com/lodging/1000000/30000/22900/22894/w4000h2664x0y0-b7d636ba_y.jpg) ### Sheraton Maui Resort & Spa 10/10 Excellent "beautiful views and good location." [](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information) ![AEI at Maui Kaanapali Villas Resort](//images.trvl-media.com/lodging/58000000/57720000/57713500/57713484/6bf5bf4d_y.jpg) ### AEI at Maui Kaanapali Villas Resort 10/10 Excellent "It was soo relaxing and clean. I had a hard time being able to check in early but after our stay we had such a great time there. Loved it would definitely come back again" [](https://expedia.ca/Lahaina-Hotels-AEI-At-Maui-Kaanapali-Villas-Resort.h57713484.Hotel-Information) ## Find out more about Upcountry Maui ## Upcountry Maui Cottages information | Number of reviews | | | --- | --- | | Accommodation | Cottages | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### How much do cottages in Upcountry Maui cost? > You'll pay between and per night for cottages in Upcountry Maui. No matter your budget, a terrific stay is only a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### How many cottages are there in Upcountry Maui? > Upcountry Maui has cottages on offer. Click on your travel dates, enter your destination and start planning your perfect trip today. ### Why book your cottage in Upcountry Maui with Expedia? > Booking a cottage in Upcountry Maui is as simple as deciding on your travel dates and choosing an ideal place for a vacation in nature. From chic retreats to affordable stays and cottages that include perks like a pool, Expedia has something for all tastes and styles. As for the best offers around? We've got you covered! ### How can I find cheap cottages in Upcountry Maui? > A wonderful way to track down cheap cottages in Upcountry Maui is with Expedia's user-friendly filter tool. 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