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Upcountry Maui Hotel Guide - Hotels with Pool in Upcountry Maui, Hawaii
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Our top choices for Upcountry Maui hotels with a pool
8.6 out of 10, Excellent, (209)
"The staff were kind and helpful. The rooms were comfortable and the property is gorgeous and well maintained. "
Sarah Catherine
The price is €546
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16Makawao
10.0 out of 10, Exceptional, (71)
"We had an amazing vacation here. We had 4 generations ranging from 4 months to 81 years and everyone had a great time. There was room to spread out and room to all gather together. Having the private pool and spa was perfect. Host was available when we needed her and the B and B was well stocked. We also loved the Maui feel of the accommodations and being out of the busier parts of Maui. I highly recommend this venue for larger groups! "
Kari L.
The price is €2,770
includes taxes & fees
6 Jan - 7 Jan 2026
8.4 out of 10, Very good, (1579)
"Excellent resort environment, Beautiful beach and nice staff. "
dewei
The price is €279
includes taxes & fees
4 Jan - 5 Jan 2026
9.6 out of 10, Exceptional, (2340)
"Always a great stay for business!!"
Stephen
The price is €287
includes taxes & fees
22 Jan - 23 Jan 2026
9.0 out of 10, Wonderful, (164)
"Very friendly staff "
Randall Kalani Apilando
The price is €367
includes taxes & fees
10 Jan - 11 Jan 2026
9.0 out of 10, Wonderful, (1193)
"Great accommodations. Beautiful location and nice staff "
Kyle
The price is €252
includes taxes & fees
13 Jan - 14 Jan 2026
7.2 out of 10, Good, (1117)
"Awesome staff awesome view couldn’t ask for more from this quaint cute hotel vibe!"
Lindsey
The price is €235
includes taxes & fees
4 Jan - 5 Jan 2026
9.0 out of 10, Wonderful, (1002)
"Clean room,helpful and pleasant staff, good food in the Bistro, quiet, comfortable room."
Deborah
The price is €370
includes taxes & fees
2 Jan - 3 Jan 2026
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.
Top Upcountry Maui Hotel Reviews
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