Title: 5 Stars Hotels in Upcountry Maui, Hawaii from CA $594 - 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) ![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) ![](https://images.trvl-media.com/place/501684/8ed15285-d20f-4fe9-81f0-3e0e3c2f92b8.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 [Jan 21 - Jan 22](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-21&endDate=2026-01-22&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 22 - Jan 23](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-22&endDate=2026-01-23&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-30&endDate=2026-02-01&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) ![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) ![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) ![Garden](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/fc34a73e.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 $1,114 CA $1,412 total includes taxes & fees Feb 17 - Feb 18 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/04e581f6.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) ![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 (1,006 reviews) "Beautiful Resort " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOANN CA $980 CA $1,253 total includes taxes & fees Feb 6 - Feb 7 [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/e41d1b6b.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 (1,005 reviews) "Wonderful staff and facility" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheila CA $1,304 CA $1,630 total includes taxes & fees Feb 3 - Feb 4 [](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) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/2e099de6.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) ### The Ritz-Carlton Maui, Kapalua [](https://www.expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) Kapalua 9.0/10 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 $1,244 CA $1,566 total includes taxes & fees Jan 22 - Jan 23 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/c7f2266e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Hotel Wailea, Relais & Chateaux - Adults Only [](https://www.expedia.ca/Kihei-Hotels-Hotel-Wailea.h85412.Hotel-Information) Wailea 9.4/10 Exceptional (1,002 reviews) "Everything was exceptional! Great property, quiet and peaceful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdulla CA $1,328 CA $1,659 total includes taxes & fees Feb 3 - Feb 4 [](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) ![Grand Residence,4 Bedroom, Premier Ocean View](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/d7321b47.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 (205 reviews) "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 $1,594 CA $2,062 total includes taxes & fees Feb 11 - Feb 12 [](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) ![Sport court](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/e26690eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/4fa117ad.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 $2,830 CA $3,449 total includes taxes & fees Feb 10 - Feb 11 [](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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/de6822ab.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 $664 CA $862 total includes taxes & fees Jan 22 - Jan 23 [](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) ![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) ![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) ### 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 $4,979 CA $5,992 total includes taxes & fees Feb 4 - Feb 5 [](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 | Private kitchen](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/05b0fbe2.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) ### 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 | Extra beds](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/a8f1dd90.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) ### 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 | Private kitchen](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/dac19e16.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 | 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 | 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 | 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) | Property amenity](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/be8d8dcf.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) | Property entrance](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/2730a420.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/117000000/116980000/116973100/116973003/0ec54ebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | View from room](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/e5bedc4a.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) ### 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) | Front of property](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/a14d66bd.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) | Property entrance](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/ab64fe5f.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/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) | Property amenity](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/60210327.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) | Property entrance](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/b38e3c9c.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 $92,146 CA $109,908 total includes taxes & fees Feb 11 - Feb 12 [](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) | Terrace/patio](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/b347d532.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) ### 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) ![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) ![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) ### 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 $663 CA $867 total Feb 21 - Feb 22 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 $657 CA $860 total Feb 3 - Feb 4 includes taxes & fees 8.6/10 Excellent! (1,008 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 $459 CA $594 total Feb 17 - Feb 18 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=22%2F01%2F2026&endDate=23%2F01%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=22%2F01%2F2026&endDate=23%2F01%2F2026®ionId=553248621593965869&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F01%2F2026&endDate=23%2F01%2F2026®ionId=553248621593965869&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F01%2F2026&endDate=23%2F01%2F2026®ionId=553248621593965869&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F01%2F2026&endDate=23%2F01%2F2026®ionId=553248621593965869&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F01%2F2026&endDate=23%2F01%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=2026-02-04&endDate=2026-02-05&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 ![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 "Great staff and service " [](https://expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.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 "Beautiful Resort " [](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.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 "Fantastic experience all around." [](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 "Yes " [](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 $594 ### 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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