Title: Book the Best ROMANTIC Hotels in Upcountry Maui, HI from CA $345  - Upcountry Maui Romantic Getaways | Expedia.ca

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![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.
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Photo by Project Forever

# Find Romantic Hotels in Upcountry Maui, HI from CA $345

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## Check availability on Upcountry Maui Romantic Hotels

Tonight

[Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-22&endDate=2025-12-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

Tomorrow

[Dec 23 - Dec 24](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-23&endDate=2025-12-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

This weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

## Our top choices for Upcountry Maui romantic hotels

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23270000/23269000/23268927/02fc15e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23270000/23269000/23268927/d096aa40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23270000/23269000/23268927/29bbe892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23270000/23269000/23268927/41b2cb25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

[](https://www.expedia.ca/Kula-Hotels-Eco-Friendly-Modern-Home.h23268927.Hotel-Information)

Kula

10/10

Exceptional

(185)

"Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Peter A.

CA $804

CA $1,610 total

includes taxes & fees

Jan 14 - Jan 15, 2026

[](https://www.expedia.ca/Kula-Hotels-Eco-Friendly-Modern-Home.h23268927.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/812b5cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/3bb1e088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/621c8ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/c43912da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!

[](https://www.expedia.ca/Makawao-Hotels-PERMITTED-Charming-LOG-HOUSE-In-REAL-Upcountry-Maui-Magical-And-Peaceful.h18955617.Hotel-Information)

Makawao

10/10

Exceptional

(50)

"Eve and her family were incredibly kind and welcoming. The property was better than we hoped with ample space for the kids to explore. We loved our stay and would come back!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jessica S.

CA $1,961

CA $3,617 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Makawao-Hotels-PERMITTED-Charming-LOG-HOUSE-In-REAL-Upcountry-Maui-Magical-And-Peaceful.h18955617.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/8a8031c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/743611fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, white sand, beach cabanas, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/4bd12a57.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/1000000/40000/34800/34767/f844108d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Royal Lahaina Resort & Bungalows

[](https://www.expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information)

Lahaina

8.4/10

Very good

(1581)

"Excellent resort environment, Beautiful beach and nice staff. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

dewei

CA $354

CA $494 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/21000000/20370000/20360600/20360538/4d656464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20370000/20360600/20360538/017bcdb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20370000/20360600/20360538/dd93f452.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/21000000/20370000/20360600/20360538/4fe21145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens

[](https://www.expedia.ca/Hana-Hotels-Paradise-Ocean-View-Cottage-Solar-Power-Tropical-Flower-Farm.h20360538.Hotel-Information)

Hana

10/10

Exceptional

(495)

"This is a beautiful place to stay. You are in the forest so there may be a bug or two. It was perfect for privacy and close to everything Hana "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie H.

CA $342

CA $610 total

includes taxes & fees

Jan 22 - Jan 23, 2026

[](https://www.expedia.ca/Hana-Hotels-Paradise-Ocean-View-Cottage-Solar-Power-Tropical-Flower-Farm.h20360538.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/d9caacb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Queen Beds, Oceanfront](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/604145df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/92e297af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/63ca0e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maui Beach Hotel

[](https://www.expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information)

Kahului

7.2/10

Good

(1118)

"Awesome staff awesome view couldn’t ask for more from this quaint cute hotel vibe!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lindsey

CA $263

CA $345 total

includes taxes & fees

Jan 20 - Jan 21, 2026

[](https://www.expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2280000/2273000/2272947/5ff4e9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![42-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/3000000/2280000/2273000/2272947/w1500h995x0y0-69eaee97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/3000000/2280000/2273000/2272947/5fcb590b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/3000000/2280000/2273000/2272947/2c9c4b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paia Inn

[](https://www.expedia.ca/Paia-Hotels-Paia-Inn.h2272947.Hotel-Information)

Paia

8.8/10

Excellent

(347)

"Very nice place and the stuffs are great!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Zhe

CA $344

CA $451 total

includes taxes & fees

Jan 18 - Jan 19, 2026

[](https://www.expedia.ca/Paia-Hotels-Paia-Inn.h2272947.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/606af9b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/7c06baf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/eeb50dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/9c5769aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

[](https://www.expedia.ca/Hana-Hotels-Beautiful-Cottage-In-The-Heart-Of-Hana.h32484007.Hotel-Information)

Hana Town Center

9.6/10

Exceptional

(191)

"Super lovely place, I wish we were staying longer! Has everything you need. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nicole

CA $407

CA $808 total

includes taxes & fees

Jan 15 - Jan 16, 2026

[](https://www.expedia.ca/Hana-Hotels-Beautiful-Cottage-In-The-Heart-Of-Hana.h32484007.Hotel-Information)

![Beach towels](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/51ee3252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/58ae806d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/25e08687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/a42f39cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fisher's Hana Bay Hale, Across from Hana Bay

[](https://www.expedia.ca/Hana-Hotels-Fishers-Hana-Bay-Hale.h22720139.Hotel-Information)

Hana Town Center

9.6/10

Exceptional

(409)

"Wonderful place to spend a few days in paradise! Would definitely stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Steve K.

CA $269

CA $546 total

includes taxes & fees

Jan 20 - Jan 21, 2026

[](https://www.expedia.ca/Hana-Hotels-Fishers-Hana-Bay-Hale.h22720139.Hotel-Information)

![Beach towels](https://images.trvl-media.com/lodging/20000000/19660000/19651200/19651188/0b16ee80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19660000/19651200/19651188/bb7cfb8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19660000/19651200/19651188/ed259162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19660000/19651200/19651188/739cc806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

[](https://www.expedia.ca/Paia-Hotels-AC-North-Shore-Maui-PaiaKuau-BrJust-Steps-Away-To-Mamas-And-Beach.h19651188.Hotel-Information)

Kuau

9.4/10

Exceptional

(196)

"Very quiet safe place. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Monica

CA $255

CA $607 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Paia-Hotels-AC-North-Shore-Maui-PaiaKuau-BrJust-Steps-Away-To-Mamas-And-Beach.h19651188.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/34000000/33490000/33483000/33482970/7f8f329c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33490000/33483000/33482970/c892d567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33490000/33483000/33482970/0aa72530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33490000/33483000/33482970/92a6f1c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View! 

[](https://www.expedia.ca/Hana-Hotels-Hana-Kai-Maui-Oceanview-Kauiki-Corner-Amazing-View.h33482970.Hotel-Information)

Hana Town Center

9.6/10

Exceptional

(76)

"Nice easy check in. Easy access to black sand beach (not the State Park)."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brett

CA $587

CA $825 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Hana-Hotels-Hana-Kai-Maui-Oceanview-Kauiki-Corner-Amazing-View.h33482970.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-05&endDate=2026-01-06&regionId=553248621593965869&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true)

## Top Upcountry Maui Hotel Reviews

![OUTRIGGER Kaanapali Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/11600/11554/82021c2d_y.jpg)

### OUTRIGGER Kaanapali Beach Resort

10/10 Excellent

"Was an amazing resort "

[](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information)

![Hilton Vacation Club Ka'anapali Beach Maui](https://images.trvl-media.com/lodging/1000000/30000/23100/23042/7a9e8592_y.jpg)

### Hilton Vacation Club Ka'anapali Beach Maui

10/10 Excellent

"The room was amazing, very clean "

[](https://expedia.ca/Lahaina-Hotels-Kaanapali-Beach-Club.h23042.Hotel-Information)

![OUTRIGGER Honua Kai Resort & Spa](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/cc604c30_y.jpg)

### OUTRIGGER Honua Kai Resort & Spa

10/10 Excellent

"Yes. Great stay as always "

[](https://expedia.ca/Lahaina-Hotels-Honua-Kai-Resort-Spa.h2740153.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

"Great service"

[](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information)

![Sheraton Maui Resort & Spa](https://images.trvl-media.com/lodging/1000000/30000/22900/22894/w4000h2664x0y0-b7d636ba_y.jpg)

### Sheraton Maui Resort & Spa

10/10 Excellent

"Mo"

[](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.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

"Staff was courteous and very engaging."

[](https://expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information)

![Royal Lahaina Resort & Bungalows](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/8a8031c5_y.jpg)

### Royal Lahaina Resort & Bungalows

10/10 Excellent

"Room was amazing with the bungalow view. Breakfast was quick and easy and very good with an incredible view"

[](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information)

![Maui Seaside Hotel](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/b53bdaab_y.jpg)

### Maui Seaside Hotel

10/10 Excellent

"Outstanding "

[](https://expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information)

![The Westin Maui Resort & Spa, Ka'anapali](https://images.trvl-media.com/lodging/1000000/30000/25900/25837/87f76342_y.jpg)

### The Westin Maui Resort & Spa, Ka'anapali

10/10 Excellent

"A great stay, kind greetings and all kindness of hospitality! Was beautiful im all sense of views and great location to great restaurants, shopping, and most importantly the beach!🏖️ . A simple thank you for this stay and cant wait to come back! 🙏🌺"

[](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information)

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- [Hotels & Resorts for Couples in Olowalu ](https://www.expedia.ca/Olowalu-Hotels-Couples-Resorts-Hotels.0-0-d11584-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Aparthotels in Pulehu ](https://www.expedia.ca/Pulehu-Apart-Hotels.d11839-aaApartHotels.Travel-Guide-Accommodation)
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- [Hotels with Early Check-in in Wailea ](https://www.expedia.ca/Wailea-Kihei-Hotels-Hotel-With-Early-Check-In.0-n7739-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels)
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- [Flights to Maui ](https://www.expedia.ca/Cheap-Flights-To-Maui.d180073.Travel-Guide-Flights)
- [Flights from Kula ](https://www.expedia.ca/lp/flights/11587/flights-from-kula)
- [Flights from Honolulu to Maui ](https://www.expedia.ca/lp/flights/1488/180073/honolulu-to-maui)
- [Flights from Calgary to Maui ](https://www.expedia.ca/lp/flights/178245/180073/calgary-to-maui)
- [Flights from Toronto to Maui ](https://www.expedia.ca/lp/flights/178314/180073/toronto-to-maui)
- [Flights from Vancouver to Maui ](https://www.expedia.ca/lp/flights/178315/180073/vancouver-to-maui)

- [Haleakala Crater ](https://www.expedia.ca/Haleakala-Crater-Kula.d501684.Vacation-Attraction)
- [Haleakala National Park ](https://www.expedia.ca/Haleakala-National-Park-Hawaii.d507525.Vacation-Attraction)
- [Visit Kula ](https://www.expedia.ca/Kula.dx11587)
- [Maui Vacations ](https://www.expedia.ca/Maui.d180073.Destination-Travel-Guides)
- [Visit Pulehu ](https://www.expedia.ca/Pulehu.dx11839)

- [Car rentals near Haleakala Crater ](https://www.expedia.ca/Car-Rentals-In-Haleakala-Crater.d501684.Car-Rental-Guide)
- [Car rentals near Haleakala National Park ](https://www.expedia.ca/Car-Rentals-In-Haleakala-National-Park.d507525.Car-Rental-Guide)
- [Car rentals near Maui ](https://www.expedia.ca/Car-Rentals-In-Maui.d180073.Car-Rental-Guide)

- [Kula Vacation Rentals ](https://www.expedia.ca/Kula-Vacation-Rentals.d11587.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)

- [Things to do in Kula ](https://www.expedia.ca/Things-To-Do-In-Kula.d11587.Travel-Guide-Activities)

- [Book Romantic Hotels in Upcountry Maui on Expedia.com ](https://www.expedia.com/Upcountry-Maui-Hotels-Romantic-Hotel.0-0-d553248621593965869-tRomanticHotel.Travel-Guide-Filter-Hotels)