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Search Vacation Homes in Madeline Island

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Our top choices for Madeline Island vacation homes

Vacation Home in Ashland

A Cozy Getaway in Ashland
10.0 out of 10, Exceptional, (14)
"Great place and host"
United States
Dustin W.
The price is ¥23,391
¥37,552 total
includes taxes & fees
Jan 7 - Jan 8, 2026
A Cozy Getaway in Ashland
9.0 out of 10, Wonderful, (11)
"This is a nice home nestled in a beautiful wooded area. Very clean and comfortable, nice attention to detail. It’s in close proximity to Bayfield, which is a hidden gem of the Great Lakes area. We’ve been to 49 states, and this area is one of our favorites."
United States
Matt
The price is ¥32,290
¥71,523 total
includes taxes & fees
Dec 27 - Dec 28
Carriage House - Chequamegon Bay, Bayfield
9.6 out of 10, Exceptional, (15)
"Very clean, relaxing and beautiful location! "
United States
Garry H.
The price is ¥34,135
¥73,914 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Apostle Pines #4 @ Apostle Highlands Golf Course
10.0 out of 10, Exceptional, (1)
The price is ¥21,052
¥51,697 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Up North Oasis - Families & Dogs in the Bayfield Area
10.0 out of 10, Exceptional, (111)
"Beautiful views, great location and proximity to Bayfield. Loved our stay. Will be back in the fall! "
United States
Monica O.
The price is ¥66,360
¥119,966 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Lake Shore Home with private dock and large deck--1 mile from Bayfield
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 Madeline Island Hotel Reviews

Find out more about Madeline Island

Madeline Island Vacation Homes information

Number of reviews
152
Accommodation
85 Vacation Homes
Lowest Price
¥37,552
Highest Price
¥119,966