Title: 5 Stars Hotels in Upcountry Maui, Hawaii from CA $412 - 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) ![](https://mediaim.expedia.com/destination/9/01b28fa5aec642d0f16d83dbe59a5809.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Upcountry Maui, Hawaii from CA $412 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-09-24&endDate=2025-09-25&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-09-25&endDate=2025-09-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-09-26&endDate=2025-09-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-03&endDate=2025-10-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Upcountry Maui 5 Star Hotels ![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) ![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/1000000/10000/8800/8765/2d5cd1be.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) ### Fairmont Kea Lani Maui Wailea 9.4/10 Exceptional (1014) "We had great time there!" CA $1,452 CA $1,794 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![9 outdoor pools, cabanas (surcharge), sun loungers](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 Wailea 8.8/10 Excellent (1015) "Stunning resort!" CA $894 CA $1,145 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/33deff2c.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) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/ee9ea3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton Maui, Kapalua Kapalua 9.0/10 Wonderful (1009) "This hotel is " CA $1,161 CA $1,459 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) ![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) ![Game room](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/f9c45622.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) ![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) ### Four Seasons Resort Maui at Wailea Wailea 9.6/10 Exceptional (1002) "This was an exceptional property and we literally had the most amazing stay. Staff were attentive and all car journies were complkmentary. " CA $1,183 CA $1,396 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.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) ![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) ![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) ![3 restaurants, breakfast, lunch, dinner served; Regional cuisine](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/65eee840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Wailea, Relais & Chateaux - Adults Only Wailea 9.4/10 Exceptional (1002) "Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive! " CA $1,262 CA $1,570 total includes taxes & fees Oct 25 - Oct 26 [](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) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/55a663a2.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) ![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) ### Montage Kapalua Bay Lahaina 9.8/10 Exceptional (202) "Super nice " CA $1,384 CA $1,779 total includes taxes & fees Oct 14 - Oct 15 [](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) ![Kayaking](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/21935658.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) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/08db5f79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ho‘olei Villas at Grand Wailea Wailea 9.6/10 Exceptional (42) "Perfect for Families. Quite spacious and great for a relaxing Family vacation." CA $2,802 CA $3,395 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Kihei-Hotels-Hoolei-At-Grand-Wailea.h1661500.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) ![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) ![Aerial view](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/8232475d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Kea Lani Maui Villa Experience Wailea 9.8/10 Exceptional (6) "It’s a decent hotel to stay for the family." CA $3,223 CA $3,883 total includes taxes & fees Sep 28 - Sep 29 [](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 Kihei 10/10 Exceptional (4) "This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!" [](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/100000000/99780000/99778400/99778371/45c2cce5.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 Wailea 10/10 Exceptional (2) "very nice place and location 🤗" [](https://www.expedia.ca/Kihei-Hotels-Wailea-Luxury-Hilltop-Resort-Vista.h99778371.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 | Balcony](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/62eb8040.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) ### Centrally Located Elegant Vistas 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!" [](https://www.expedia.ca/Kihei-Hotels-Centrally-Located-Elegant-Vistas.h96448155.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) ![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) ![Dining](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/605dcf2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Kihei Paradise Vistas 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. " [](https://www.expedia.ca/Kihei-Hotels-Oceanfront-Kihei-Paradise-Vistas.h103891972.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/82bc9789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/d2dcf4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, 2 Bedrooms, Kitchen, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/60aecbec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/b551e971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale Luxurious Ocean Resort Vistas Kihei [](https://www.expedia.ca/Kihei-Hotels-Upscale-Luxurious-Ocean-Resort-Vistas.h102687821.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) | 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) | Beach](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/a0b26604.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/ed5ea160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206) 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 (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) | 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) ![Condo (6 Bedrooms) | Dining](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/c3352339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms)](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/f21063a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401) 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) | 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)](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/3c805d4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (Multiple Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/3f6bea75.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) 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) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/ce2adfb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/14ae217c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/1e57ae8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Living room](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/3ceccb43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### KBM Resorts Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Free Rental Car Malia-at-montage-kapalua-bay 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) | Pool](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/69ca5aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/d6f0d128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family dining](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/76262758.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) ### Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203) Kaanapali [](https://www.expedia.ca/Kaanapali-Hotels-KBM-Resorts-Free-CAR-Honua-Kai-Hkh-201203.h117434332.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/120000000/119650000/119641300/119641201/w1916h1320x0y0-78aefb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (2 Bedrooms) | View from room](https://images.trvl-media.com/lodging/120000000/119650000/119641300/119641201/acc192a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (2 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/120000000/119650000/119641300/119641201/b16258ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119650000/119641300/119641201/c545cb79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kaanapali Shores 616 Free CAR KBM Resorts Kaanapali [](https://www.expedia.ca/Kaanapali-Hotels-NEW-KBM-Resorts-Free-CAR-Kaanapali-Shores-6th-Floor-Ocean-View-Suite-Steps-To-Pool-Beach-Ks-616.h119641201.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. ![Andaz Maui at Wailea Resort - a concept by Hyatt](https://images.trvl-media.com/lodging/1000000/10000/2600/2552/487d8e2d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Andaz Maui at Wailea Resort - a concept by Hyatt 3550 Wailea Alanui Dr, Kihei, HI CA $1,175 CA $1,467 total Oct 17 - Oct 18 includes taxes & fees 9.2/10 Wonderful! (998 reviews) [](https://expedia.ca/Kihei-Hotels-Andaz-Maui-At-Wailea-Resort-A-Concept-By-Hyatt.h2552.Hotel-Information) ![Royal Lahaina Resort & Bungalows](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/8a8031c5_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Royal Lahaina Resort & Bungalows 2780 Kekaa Dr, Lahaina, HI CA $287 CA $412 total Oct 7 - Oct 8 includes taxes & fees 8.2/10 Very Good! (1,451 reviews) [](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) ![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 $674 CA $875 total Oct 2 - Oct 3 includes taxes & fees 9/10 Wonderful! (970 reviews) [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.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=25%2F09%2F2025&endDate=26%2F09%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=25%2F09%2F2025&endDate=26%2F09%2F2025®ionId=553248621593965869&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=25%2F09%2F2025&endDate=26%2F09%2F2025®ionId=553248621593965869&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=25%2F09%2F2025&endDate=26%2F09%2F2025®ionId=553248621593965869&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=25%2F09%2F2025&endDate=26%2F09%2F2025®ionId=553248621593965869&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=25%2F09%2F2025&endDate=26%2F09%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=2025-10-08&endDate=2025-10-09&adults=2®ionId=553248621593965869) ![Maui Island featuring landscape views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/37000/37724-Maui.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Upcountry Maui Hotel Reviews ![Fairmont Kea Lani Maui](//images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg) ### Fairmont Kea Lani Maui 10/10 Excellent "I like how they had a gift in our room to congratulate us on our wedding " [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![The Ritz-Carlton Maui, Kapalua](//images.trvl-media.com/lodging/1000000/10000/3400/3390/w3996h2667x0y0-f44bed53_y.jpg) ### The Ritz-Carlton Maui, Kapalua 10/10 Excellent "amazing property with great people that makes you feel home. Best service possible. Food and drink are great. Couldnt ask for a better place to stay in Maui." [](https://expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) ![Grand Wailea Maui, A Waldorf Astoria Resort](//images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997_y.jpg) ### Grand Wailea Maui, A Waldorf Astoria Resort 10/10 Excellent "Stunning resort!" [](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.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? > How much you pay for a 5-star hotel in Upcountry Maui can vary based on when you decide to travel and how long you plan to be away, among a range of factors. Use our price per night filter and other search tools to score the best deal on an indulgent stay. > > > > - Search for the lowest price per night from CA $412 ### What makes a hotel 5 stars in Upcountry Maui? > From fine dining venues and 24/7 fitness centres to pools and dreamy bedding, the 5-star experience in Upcountry Maui is all about relaxation and luxury. But it requires more than just upscale perks to earn a 5-star rating. Accommodations must also provide superior services like massage treatments, on-site dry cleaning and laundry and room service any time day or night. ### Are there any 5-star all-inclusive resorts in Upcountry Maui? > Use Expedia's filters to find a luxurious escape in Upcountry Maui where most of what you need is included. After your initial search, narrow your results for hotels that have a 5-star rating and are deemed "All inclusive." The main thing on the agenda at these stays? 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