Top Guest Houses in Upcountry Maui in 2026

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Our top choices for Upcountry Maui guest houses

The Historic Wailuku Inn

Wailuku

Linda

includes taxes & fees

8 Jun - 9 Jun

Standard Cottage, 1 Bedroom, Ocean View | View from room

Nona Lani Cottages

North Kihei

Leonard

includes taxes & fees

9 Jun - 10 Jun

JJs Hāna Hale - Farm House

Kaʻeleku

DANIEL

includes taxes & fees

15 Jun - 16 Jun

Paia Inn - 3 Bedroom Ocean Front Beach House

Paia

"This is a beautiful property in an absolutely amazing location. We love love LOVED Paia - it is away from the more touristy areas of Maui, has great shops and restaurants, and it was so incredible to be directly on the beach while also being smack in the middle of town. When I booked, I did not realize that this house is part of a hotel, which made it a bit difficult to find at first, but it turned out to be great because we had the best of both worlds - our own house/space but with the...

Katy F.

includes taxes & fees

8 Jun - 9 Jun

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Top Upcountry Maui Hotel Reviews

Fairmont Kea Lani Maui

10/10 Excellent

"Property is very clean and close to the ocean. The staff were amazing and very helpful with anything we needed. They had a courtesy shuttle you can use to get around wailea."