Search Upcountry Maui Cottage Rentals from CA $305

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Browse Select Upcountry Maui Cottages

Our top choices for Upcountry Maui cottages

Adorable 1930's Gingerbread House....Permitted!

9.8 out of 10, Exceptional, (12)
"My wife and I enjoyed our stay. House is perfect for a couple and we enjoyed the animals making their rounds throughout the property each day. Eve was an outstanding hostess and made sure we had everything we needed and enjoyed our stay. If we get to Maui again, we will definitely stay in the Gingerbread House again."
The price is CA $380
CA $822 total
includes taxes & fees
Sep 7 - Sep 8
Adorable 1930's Gingerbread House....Permitted!

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

9.6 out of 10, Exceptional, (188)
"We had an amazing stay in Hana at the cottage. It’s clean and well equipped. Beautiful view from the kitchen and bedroom. Has a nice private outdoor space. "
The price is CA $305
CA $717 total
includes taxes & fees
Sep 1 - Sep 2
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

10.0 out of 10, Exceptional, (80)
"After eight trips to Hawaii, this is the first place where I really felt I was in paradise. "
The price is CA $429
CA $750 total
includes taxes & fees
Aug 29 - Aug 30
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (265)
"We had a good time, thanks for sharing your place. "
The price is CA $408
CA $770 total
includes taxes & fees
Sep 1 - Sep 2
Secluded cottage on Tropical flower farm

Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops

10.0 out of 10, Exceptional, (71)
"This charming cottage is a marvel of great design, surrounded by a beautiful garden. We enjoyed walking through the friendly neighborhood on our way to town. The owners are skilled, organized inn keepers. All contributed to a wonderful week on Maui."
The price is CA $415
CA $770 total
includes taxes & fees
Sep 15 - Sep 16
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops

Beach Bungalow + Bikes & Pickleball Gear

9.2 out of 10, Wonderful, (10)
"We often had the pool to ourselves, occasionally sharing it with at most one other family. The location is convenient and it was easy to get to many different beaches. One thing to be aware of: the loft ceiling is quite low and the space there is tight. The extra twin rollout bed is at the floor level. "
The price is CA $380
CA $1,206 total
includes taxes & fees
Aug 31 - Sep 1
Beach Bungalow + Bikes & Pickleball Gear
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.
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Top Upcountry Maui Hotel Reviews