Title: 5 Stars Hotels in Upcountry Maui, Hawaii from CA $648 - 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 ![](https://images.trvl-media.com/place/507525/451f5c7a-2ae1-4683-8787-8d1827405b60.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 5 - Feb 6](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-02-05&endDate=2026-02-06&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-02-06&endDate=2026-02-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-02-06&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-02-13&endDate=2026-02-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Upcountry Maui 5-star hotels ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/b7f4e2f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Garden](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/fc34a73e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/9260ff25.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 (1,001 reviews) "Service was good" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) kathy CA $1,085 CA $1,377 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) ![9 outdoor pools, cabanas (surcharge), sun loungers](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/1191869f.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) ![Executive lounge](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/6950a9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/5e906169.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 (1,004 reviews) "Beautiful Resort " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOANN CA $966 CA $1,235 total includes taxes & fees Feb 24 - Feb 25 [](https://www.expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/299cd4dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/e41d1b6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, swim-up bar, poolside bar](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/df893a7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/993251db.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 (1,002 reviews) "Wonderful staff and facility" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheila CA $1,251 CA $1,566 total includes taxes & fees Feb 24 - Feb 25 [](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/bb9d5140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/6d18f4dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/2e099de6.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 (1,001 reviews) "Top notch property with amazing service and staff" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Delaine CA $1,431 CA $1,787 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/d048b5ef.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/bab75c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/c7f2266e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/e05816aa.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 (1,001 reviews) "Everything was exceptional! Great property, quiet and peaceful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdulla CA $1,383 CA $1,722 total includes taxes & fees Mar 6 - Mar 7 [](https://www.expedia.ca/Kihei-Hotels-Hotel-Wailea.h85412.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/3cb35af4.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) ![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) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/f18fc3b9.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 (206 reviews) "The views are next level. We enjoyed the pools, spa, restaurant and more. It was our second stay there and definitely going back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mandy D CA $1,505 CA $1,948 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Lahaina-Hotels-Montage-Kapalua-Bay.h5914192.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/3bd64cf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/642c07c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/e26690eb.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) ### 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 reviews) "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 $2,768 CA $3,375 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Kihei-Hotels-Hoolei-At-Grand-Wailea.h1661500.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/7c8ded28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/de6822ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, Oceanfront (Royal Bungalow)](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/a73e158c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/d996ca06.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 9.4/10 Exceptional (3 reviews) "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 $636 CA $827 total includes taxes & fees Mar 3 - Mar 4 [](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/e9c2591c.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) ![2 bars/lounges, swim-up bar, poolside bar](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/eb7843a7.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 reviews) "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 $4,637 CA $5,585 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui-Villa-Experience.h37220226.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/b097c053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/c3c04654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Living area](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/49922dc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Private kitchen](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/05b0fbe2.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 (7 reviews) "The condo was very clean, loved all of the decor, was very beautiful. Had everything you could possibly need in kitchen and bathrooms. Would definitely stay again! Everyone we talked to was very nice and helpful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paulina [](https://www.expedia.ca/Kihei-Hotels-2-2-Oceanview-Modern-Resort-Vistas.h100963582.Hotel-Information) ![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) ![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 | Extra beds](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/a3ffbcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment | Extra beds](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/a8f1dd90.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 reviews) "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) ![Luxury Apartment, Ocean View | Living area](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/c44f01d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, Ocean View | Living area](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/e6bf99f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, Ocean View | Balcony](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/ce85adf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, Ocean View | Extra beds](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/675849fa.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 reviews) "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 | Living area](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/6ed677aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Living area](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/977a4de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/97000000/96450000/96448200/96448155/570ec027.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 review) "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) | Property entrance](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/1c66b6c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | View from room](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/5f131f25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Property entrance](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/2730a420.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) ### 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 entrance](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/2c93332e.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/117000000/116980000/116973100/116973003/362be129.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) | Property entrance](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/0831c2c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Property entrance](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/00110a5a.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) | View from room](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/f095a3df.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) | Property entrance](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/76a3d357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | View from room](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/cc04f5b2.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) | Property amenity](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/dbe769d9.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) | Property entrance](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/fd558606.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) ![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) | Property amenity](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/60210327.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 CA $91,051 CA $108,599 total includes taxes & fees Feb 25 - Feb 26 [](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) ![Outdoor pool, a waterfall pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/d3669f53.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/ea9e6d95.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) | Terrace/patio](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/b347d532.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/eece75dd.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) | Property entrance](https://images.trvl-media.com/lodging/120000000/119820000/119813300/119813208/281edb66.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 $640 CA $838 total Mar 1 - Mar 2 includes taxes & fees 9/10 Wonderful! (1,001 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 $522 CA $699 total Mar 8 - Mar 9 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 Feb 28 - Mar 1 includes taxes & fees 8.8/10 Excellent! (1,001 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=06%2F02%2F2026&endDate=07%2F02%2F2026®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=06%2F02%2F2026&endDate=07%2F02%2F2026®ionId=553248621593965869&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F02%2F2026&endDate=07%2F02%2F2026®ionId=553248621593965869&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F02%2F2026&endDate=07%2F02%2F2026®ionId=553248621593965869&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F02%2F2026&endDate=07%2F02%2F2026®ionId=553248621593965869&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F02%2F2026&endDate=07%2F02%2F2026®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=2026-02-19&endDate=2026-02-20&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 ![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 "The room was always clean. Susie at the front desk was so helpful and kind. I’ll be coming back" [](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 "Simply fantastic!!!!!!!!!" [](https://expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.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 "All around amazing experience. Gorgeous setting, great amenities, our trip went off without a hitch. " [](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 "Wonderful Staff, Chef Ignacio at Banyan Tree is the Best, Guests, Energy, Location Food, Everything was so nice. " [](https://expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.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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