Title: 5 Stars Hotels in Upcountry Maui, Hawaii from CA $455 - 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 $455 ![](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 [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-12&endDate=2025-10-13&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-24&endDate=2025-10-26&adults=2&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) ![6 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/10a00005.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 (1012) "Amazing hotel I would stay here again" CA $1,329 CA $1,651 total includes taxes & fees Oct 17 - Oct 18 [](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/1000000/10000/7900/7867/813399da.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 (1008) "Wonderful accommodations!" CA $840 CA $1,082 total includes taxes & fees Nov 13 - Nov 14 [](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) ![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) ![Beach nearby, white sand, free beach shuttle, beach cabanas](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/3545b597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, 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) ### The Ritz-Carlton Maui, Kapalua Kapalua 9.0/10 Wonderful (1014) "Every please the staff was great. the room was clean on a daily the staff every helpful. " CA $1,161 CA $1,461 total includes taxes & fees Oct 30 - Oct 31 [](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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/a0a6da1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Resort Maui at Wailea Wailea 9.6/10 Exceptional (1006) "Beautiful resort. Everything was absolutely perfect. Room was impeccable. Staff were very friendly and accommodating. Pool and beach area were really nice. Will stay here again. " CA $1,057 CA $1,247 total includes taxes & fees Oct 14 - Oct 15 [](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) ![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) ![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 $1,235 CA $1,539 total includes taxes & fees Oct 19 - Oct 20 [](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) ![Lobby](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/523d64b7.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) ### Montage Kapalua Bay Lahaina 9.6/10 Exceptional (203) "We used Spa, expedia mentioned there is 20% discount and we didn't get it" CA $1,401 CA $1,801 total includes taxes & fees Nov 3 - Nov 4 [](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) ![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) ![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 Wailea 9.6/10 Exceptional (43) "Perfect for Families. Quite spacious and great for a relaxing Family vacation." CA $2,784 CA $3,375 total includes taxes & fees Oct 23 - Oct 24 [](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) ![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) ![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) ### Fairmont Kea Lani Maui Villa Experience Wailea 9.8/10 Exceptional (6) "It’s a decent hotel to stay for the family." CA $4,046 CA $4,855 total includes taxes & fees Nov 9 - Nov 10 [](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) ![Exterior](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/98e97d7a.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) ### 2 2 Oceanview Modern Resort Vistas Central Kihei 10/10 Exceptional (5) "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 | 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 | 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 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 | 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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/d5c0e23e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centrally Located Elegant Vistas 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!" [](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 | Living area](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/c44f01d6.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](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 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. " [](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) ![Luxury Apartment, 2 Bedrooms, Kitchen, Ocean View | Living area](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/6e2825db.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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/d2dcf4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale Luxurious Ocean Resort Vistas South 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) | Property entrance](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/ed5ea160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/c4565a15.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)](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/f21063a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Beach](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/9caadc5f.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) 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) | 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)](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) | Dining](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973017/w1586h1066x14y0-ed8b935e.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) ![Condo (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/d5403ae8.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) ![Condo (3 Bedrooms)](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/ae884368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/5b46714a.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) ![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) | Living room](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434332/3adc0658.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) ### 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) ![Condo (2 Bedrooms) | Pool](https://images.trvl-media.com/lodging/120000000/119650000/119641300/119641201/5070c875.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) | View from room](https://images.trvl-media.com/lodging/120000000/119650000/119641300/119641201/82c2eb86.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) ### NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach! Ks-616 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 $1,482 total Oct 26 - Oct 27 includes taxes & fees 9.2/10 Wonderful! (997 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 $323 CA $455 total Nov 3 - Nov 4 includes taxes & fees 8.4/10 Very Good! (1,468 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 $609 CA $800 total Oct 15 - Oct 16 includes taxes & fees 9/10 Wonderful! (990 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=14%2F10%2F2025&endDate=15%2F10%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=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248621593965869&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248621593965869&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248621593965869&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248621593965869&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%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=2025-10-27&endDate=2025-10-28&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 ![Grand Wailea Maui, A Waldorf Astoria Resort](//images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997_y.jpg) ### Grand Wailea Maui, A Waldorf Astoria Resort 10/10 Excellent "The property is beautiful " [](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ![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 "Very good" [](https://expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) ![Four Seasons Resort Maui at Wailea](//images.trvl-media.com/lodging/1000000/20000/14400/14336/ed7cc193_y.jpg) ### Four Seasons Resort Maui at Wailea 10/10 Excellent "Wonderful!" [](https://expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) ![Fairmont Kea Lani Maui](//images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg) ### Fairmont Kea Lani Maui 10/10 Excellent "Room had a lovely ocean view. Service was superb. The lobby and grounds are magnificent! Great food. This is the best hotel in Maui now. " [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.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 $455 ### 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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