Title: 5 Stars Hotels in Upcountry Maui, Hawaii from CA $641 - Find Cheap Upcountry Maui Hotels With 5 Stars | 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) ![View over Haleakala crater, at 3000 ft. Make sure that the skies are clear before heading to Haleakala, otherwise this view could be totally blocked by clouds. #AboveItAll](https://images.trvl-media.com/place/507525/451f5c7a-2ae1-4683-8787-8d1827405b60.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Project Forever # 5 Stars Hotels in Upcountry Maui, Hawaii from CA $641 - ![](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 availability on Upcountry Maui 5 Star Hotels Tonight [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-26&endDate=2025-12-27&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-27&endDate=2025-12-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Upcountry Maui 5-star hotels ![Club Ocean Front One Bedroom Suite](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/ed7cc193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Maile Three-Bedroom Presidential Suite](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/2cdd56af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/0069cac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/f9c45622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Resort Maui at Wailea [](https://www.expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) Wailea 9.6/10 Exceptional (1000) "Beautiful property, efficient staff, truly a wonderful stay " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Angela CA $1,087 CA $1,291 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) ![7 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/8788f08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/23013212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/w3837h2557x3y3-5ebfbeb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Wailea Maui, A Waldorf Astoria Resort [](https://www.expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) Wailea 8.8/10 Excellent (1002) "Very nice resort for a family vacation!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashwini CA $937 CA $1,201 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/b17d91a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/e8ef7f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, 1 Bedroom, Kilohana Corner Suite, (1 King Bed) | Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/04bfdd03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Kea Lani Maui [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) Wailea 9.4/10 Exceptional (1000) "Wonderful staff and facility" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheila CA $1,173 CA $1,473 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![3 outdoor pools, cabanas (surcharge), sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/w3996h2667x0y0-f44bed53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, white sand, free beach shuttle, beach cabanas](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/863b2be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 restaurants, breakfast, lunch, dinner served; seafood](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/99ce1291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/33deff2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton Maui, Kapalua [](https://www.expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) Kapalua 9.2/10 Wonderful (1001) "Top notch property with amazing service and staff" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Delaine CA $1,093 CA $1,386 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/51e44f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/d4acdf82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Regional cuisine](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/ee7d62b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/887fcb78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Wailea, Relais & Chateaux - Adults Only [](https://www.expedia.ca/Kihei-Hotels-Hotel-Wailea.h85412.Hotel-Information) Wailea 9.4/10 Exceptional (1001) "Staff was great and the property was stunning. It was everything we wanted for our honeymoon. Other couples mentioned " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob CA $1,435 CA $1,784 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Kihei-Hotels-Hotel-Wailea.h85412.Hotel-Information) ![On the beach, beach towels, snorkeling, surfing](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/a0787557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/c3ab62d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch served, American cuisine, pool views ](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/58212487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/523d64b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montage Kapalua Bay [](https://www.expedia.ca/Lahaina-Hotels-Montage-Kapalua-Bay.h5914192.Hotel-Information) Lahaina 9.6/10 Exceptional (204) "We used Spa, expedia mentioned there is 20% discount and we didn't get it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ronak CA $1,919 CA $2,483 total includes taxes & fees Jan 26 - Jan 27, 2026 [](https://www.expedia.ca/Lahaina-Hotels-Montage-Kapalua-Bay.h5914192.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/0e84672f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/w3837h2207x3y3-85d53f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/4f26861d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Kayaking](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/21935658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ho‘olei Villas at Grand Wailea [](https://www.expedia.ca/Kihei-Hotels-Hoolei-At-Grand-Wailea.h1661500.Hotel-Information) Wailea 9.6/10 Exceptional (44) "Perfect for Families. Quite spacious and great for a relaxing Family vacation." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $2,737 CA $3,338 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Kihei-Hotels-Hoolei-At-Grand-Wailea.h1661500.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/w5464h3630x0y5-53069acf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach cabanas, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/42b84055.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/4021aaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/231f7809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Royal Lahaina Bungalows & Spa [](https://www.expedia.ca/Lahaina-Hotels-Royal-Lahaina-Bungalows-Spa.h115794140.Hotel-Information) Lahaina 9.0/10 Wonderful (2) "Clean room and staff is super friendly. Would stay here again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rene CA $479 CA $641 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Lahaina-Hotels-Royal-Lahaina-Bungalows-Spa.h115794140.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/c0b8dfb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/03d12ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/8232475d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/29664a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Kea Lani Maui Villa Experience [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui-Villa-Experience.h37220226.Hotel-Information) Wailea 9.8/10 Exceptional (6) "It’s a decent hotel to stay for the family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sze Wai CA $3,951 CA $4,741 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui-Villa-Experience.h37220226.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/f537c1fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Living area](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/a0ab1941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Living area](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/c6acb995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/98e97d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 2 Oceanview Modern Resort Vistas [](https://www.expedia.ca/Kihei-Hotels-2-2-Oceanview-Modern-Resort-Vistas.h100963582.Hotel-Information) Central Kihei 9.8/10 Exceptional (6) "This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jarrod [](https://www.expedia.ca/Kihei-Hotels-2-2-Oceanview-Modern-Resort-Vistas.h100963582.Hotel-Information) ![Luxury Apartment | Private kitchen](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/46d854e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment | Living area](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/56fbfac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment | Private kitchen](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/53237f33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment | Beach/ocean view](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/725c39a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wailea Luxury Hilltop Resort Vistas [](https://www.expedia.ca/Kihei-Hotels-Wailea-Luxury-Hilltop-Resort-Vista.h99778371.Hotel-Information) Wailea 10/10 Exceptional (2) "very nice place and location 🤗" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maryna [](https://www.expedia.ca/Kihei-Hotels-Wailea-Luxury-Hilltop-Resort-Vista.h99778371.Hotel-Information) ![Outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/aaadbf4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/605dcf2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/dac19e16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, Ocean View](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/0b8f6070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Kihei Paradise Vistas [](https://www.expedia.ca/Kihei-Hotels-Oceanfront-Kihei-Paradise-Vistas.h103891972.Hotel-Information) Central Kihei 10/10 Exceptional (2) "This property was clean, quiet, and had excellent security. The barbecue grill was easy to use. They had sandless beach towels, which worked so well. The view was beautiful! I want to go again next year. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mae [](https://www.expedia.ca/Kihei-Hotels-Oceanfront-Kihei-Paradise-Vistas.h103891972.Hotel-Information) ![Luxury Condo | Balcony](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/26b6bec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Private kitchen](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/4d0d378f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Extra beds](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/7861cddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Balcony](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/62eb8040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centrally Located Elegant Vistas [](https://www.expedia.ca/Kihei-Hotels-Centrally-Located-Elegant-Vistas.h96448155.Hotel-Information) South Kihei 10/10 Exceptional (1) "Love this Kihei home! Centrally located! It is very clean. We love that they have beach chairs and towels on hand. Overall great experience stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edwin [](https://www.expedia.ca/Kihei-Hotels-Centrally-Located-Elegant-Vistas.h96448155.Hotel-Information) ![Condo (3 Bedrooms) | Pool](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/c4870c78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/81031374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Beach](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/e4b0acbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Dining](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/c232b144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### KBM Resorts Free CAR Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Mon-5203 [](https://www.expedia.ca/Kapalua-Hotels-KBM-Resorts-Luxury-Oceanfront-Villa-At-Montage-Kapalua-Bay-Private-Lanai-And-BBQ-Free-Rental-Car-Malia-At-Montage-Kapalua-Bay.h119312427.Hotel-Information) Kapalua [](https://www.expedia.ca/Kapalua-Hotels-KBM-Resorts-Luxury-Oceanfront-Villa-At-Montage-Kapalua-Bay-Private-Lanai-And-BBQ-Free-Rental-Car-Malia-At-Montage-Kapalua-Bay.h119312427.Hotel-Information) ![Condo (6 Bedrooms) | Property entrance](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/a977472e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/362be129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/0ec54ebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/3b4ba262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206) [](https://www.expedia.ca/Kapalua-Hotels-Spacious-6-Bedroom-Montage-Kapalua-Collection-Multi-Unit-Listing-Same-Floor-Ocean-Views-2-Free-Rental-Cars-Mon-22042206.h116973003.Hotel-Information) Kapalua [](https://www.expedia.ca/Kapalua-Hotels-Spacious-6-Bedroom-Montage-Kapalua-Collection-Multi-Unit-Listing-Same-Floor-Ocean-Views-2-Free-Rental-Cars-Mon-22042206.h116973003.Hotel-Information) ![Condo (3 Bedrooms) | Pool](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/8d834930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/d56dba91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Beach](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/95de64d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms)](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/e77c7ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW KBM Resorts Free CAR Hale Nalu At Montage Kapalua Bay, Sleeps 10! Oceanfront 3-bedroom Condo With Daily Housekeeping, Spa! Mon-6302 [](https://www.expedia.ca/NEW-KBM-Resorts-Free-CAR-Hale-Nalu-At-Montage-Kapalua-Bay.h119719148.Hotel-Information) Kapalua [](https://www.expedia.ca/NEW-KBM-Resorts-Free-CAR-Hale-Nalu-At-Montage-Kapalua-Bay.h119719148.Hotel-Information) ![Condo (6 Bedrooms) | Pool](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/c9696859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/dbe769d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/18cf5610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Terrace/patio](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/w1918h1280x0y0-cb6a6863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401) [](https://www.expedia.ca/Kapalua-Hotels-Spacious-6-Bedroom-Montage-Kapalua-Collection-Multi-Unit-Listing-Different-Floors-Ocean-Views-2-Free-Rental-Cars-Mon-63016401.h116973002.Hotel-Information) Kapalua [](https://www.expedia.ca/Kapalua-Hotels-Spacious-6-Bedroom-Montage-Kapalua-Collection-Multi-Unit-Listing-Different-Floors-Ocean-Views-2-Free-Rental-Cars-Mon-63016401.h116973002.Hotel-Information) ![Condo (Multiple Bedrooms) | Pool](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/a4362ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (Multiple Bedrooms) | View from room](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/a1963e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (Multiple Bedrooms) | Beach](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/07c4c6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (Multiple Bedrooms) | View from room](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/d3adc05e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304) [](https://www.expedia.ca/Kapalua-Hotels-Spacious-9-Bedroom-Montage-Kapalua-Collection-Multi-Unit-Listing-Same-Enclave-Ocean-Views-3-Free-Rental-Cars-Mon-1205.h116973017.Hotel-Information) Kapalua [](https://www.expedia.ca/Kapalua-Hotels-Spacious-9-Bedroom-Montage-Kapalua-Collection-Multi-Unit-Listing-Same-Enclave-Ocean-Views-3-Free-Rental-Cars-Mon-1205.h116973017.Hotel-Information) ![Condo (6 Bedrooms) | Pool](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/88d456c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Beach](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/ae711b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Dining](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/ae9661a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Property entrance](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/cc9ec020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203) [](https://www.expedia.ca/Kaanapali-Hotels-KBM-Resorts-Free-CAR-Honua-Kai-Hkh-201203.h117434332.Hotel-Information) Kaanapali [](https://www.expedia.ca/Kaanapali-Hotels-KBM-Resorts-Free-CAR-Honua-Kai-Hkh-201203.h117434332.Hotel-Information) ![Condo (3 Bedrooms) | Pool](https://images.trvl-media.com/lodging/120000000/119820000/119813300/119813208/cb153010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Property entrance](https://images.trvl-media.com/lodging/120000000/119820000/119813300/119813208/281edb66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/120000000/119820000/119813300/119813208/9e47af18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/120000000/119820000/119813300/119813208/892ea055.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Honua Kai Konea 2 Free Rental Cars KBM Resorts Family Friendly 2 Units, 3 Bedrooms Ml-1436 [](https://www.expedia.ca/Kaanapali-Hotels-KBM-Resorts-Spacious-3-Bedroom-Honua-Kai-Collection-Multi-Unit-Listing-Same-Floor-2-Free-Rental-Cars-Hkk-70630.h119813208.Hotel-Information) Kaanapali [](https://www.expedia.ca/Kaanapali-Hotels-KBM-Resorts-Spacious-3-Bedroom-Honua-Kai-Collection-Multi-Unit-Listing-Same-Floor-2-Free-Rental-Cars-Hkk-70630.h119813208.Hotel-Information) ![](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%2F5Star-Upcountry-Maui-Hotels.s50-0-d553248621593965869.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Upcountry-Maui-Hotels.s50-0-d553248621593965869.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Upcountry Maui. ![The Westin Maui Resort & Spa, Ka'anapali](https://images.trvl-media.com/lodging/1000000/30000/25900/25837/87f76342_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Westin Maui Resort & Spa, Ka'anapali 2365 Kaanapali Pkwy Lahaina HI CA $659 CA $862 total Jan 4 - Jan 5, 2026 includes taxes & fees 9/10 Wonderful! (1,008 reviews) [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information) ![Sheraton Maui Resort & Spa](https://images.trvl-media.com/lodging/1000000/30000/22900/22894/w4000h2664x0y0-b7d636ba_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sheraton Maui Resort & Spa 2605 Kaanapali Pkwy Lahaina HI CA $655 CA $857 total Jan 20 - Jan 21, 2026 includes taxes & fees 8.6/10 Excellent! (1,004 reviews) [](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information) ![Hilton Vacation Club Ka'anapali Beach Maui](https://images.trvl-media.com/lodging/1000000/30000/23100/23042/7a9e8592_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton Vacation Club Ka'anapali Beach Maui 104 Ka'anapali Shores Place Kaanapali HI CA $505 CA $648 total Jan 18 - Jan 19, 2026 includes taxes & fees 8.8/10 Excellent! (1,002 reviews) [](https://expedia.ca/Lahaina-Hotels-Kaanapali-Beach-Club.h23042.Hotel-Information) Still don't see what you're looking for? [See all properties in Upcountry Maui.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=553248621593965869&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=553248621593965869&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=553248621593965869&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=553248621593965869&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=553248621593965869&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=553248621593965869&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Upcountry Maui Head to sights like Haleakalā Visitor Center and Haleakala Crater as you discover Upcountry Maui—a relaxing area also known for its island views. [See all hotels in Upcountry Maui](https://www.expedia.ca/Hotel-Search?startDate=2026-01-09&endDate=2026-01-10&adults=2®ionId=553248621593965869) ![View over Haleakala crater, at 3000 ft. Make sure that the skies are clear before heading to Haleakala, otherwise this view could be totally blocked by clouds. #AboveItAll](https://images.trvl-media.com/place/507525/451f5c7a-2ae1-4683-8787-8d1827405b60.jpg?impolicy=fcrop&w=899&h=600&p=1&q=high) Photo by Project Forever ## Top Upcountry Maui Hotel Reviews ![Fairmont Kea Lani Maui](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg) ### Fairmont Kea Lani Maui 10/10 Excellent "Room setup was great, pools and beach were excellent. Everyone had a great time" [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![The Ritz-Carlton Maui, Kapalua](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/w3996h2667x0y0-f44bed53_y.jpg) ### The Ritz-Carlton Maui, Kapalua 10/10 Excellent "Top notch property with amazing service and staff" [](https://expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) ![Grand Wailea Maui, A Waldorf Astoria Resort](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997_y.jpg) ### Grand Wailea Maui, A Waldorf Astoria Resort 10/10 Excellent "Unbelievable experience." [](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ![Four Seasons Resort Maui at Wailea](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/ed7cc193_y.jpg) ### Four Seasons Resort Maui at Wailea 10/10 Excellent "Always exceptional " [](https://expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) ## Find out more about Upcountry Maui Luxury is the name of the game at the best 5 Stars hotels in Upcountry Maui. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Upcountry Maui 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Upcountry Maui hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Upcountry Maui without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Upcountry Maui. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Upcountry Maui? > - Search for the lowest price per night from CA $648 ### What makes a hotel 5 stars in Upcountry Maui? ### Are there any 5-star all-inclusive resorts in Upcountry Maui? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Maui ](https://www.expedia.ca/1Star-Maui-Hotels.s10-0-d180073.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Kahului ](https://www.expedia.ca/2Star-Kahului-Hotels.s20-0-d2646.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Kihei ](https://www.expedia.ca/2Star-Kihei-Hotels.s20-0-d9304.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Kuau ](https://www.expedia.ca/2Star-Kuau-Hotels.s20-0-d553248635975748672.Travel-Guide-Filter-Hotels) - 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