A rocky shoreline with clear water, a small tree on a rock formation, and lush greenery.

Holiday Homes in Madeline Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Madeline Island holiday homes

A round table with a dark tablecloth and a decorative piece on it, surrounded by wooden chairs. A large window offers a view of a body of water and trees.

1. Lake Shore Home with private dock and large deck--1 mile from Bayfield

Lake Shore Home with private dock and large deck--1 mile from Bayfield
Bayfield
10.0 out of 10, Exceptional, (124 reviews)
"Great property! wonderful rejuvenation time for myself and my family"
United States
Brian
The price is NZ$1,026
includes taxes & fees
22 Nov - 23 Nov
Lake Shore Home with private dock and large deck--1 mile from Bayfield
A hotel room with a large bed, a sitting area with a view, and a bathtub.

2. Main @ Hendrickson House

Main @ Hendrickson House
Bayfield
10.0 out of 10, Exceptional, (3 reviews)
"The house was perfect for us. Very clean and had everything we needed to enjoy a relaxing 2 day getaway. I would definitely stay here again!!"
United States
Steven A.
The price is NZ$934
includes taxes & fees
9 Nov - 10 Nov
Main @ Hendrickson House
A spacious living room with a stone fireplace, a large brown sofa, a television, and a ceiling fan.

3. Apostle Pines #4 @ Apostle Highlands Golf Course

Apostle Pines #4 @ Apostle Highlands Golf Course
Bayfield
9.8 out of 10, Exceptional, (22 reviews)
"Awesome place! Views of the golf course was amazing!"
United States
Anonymous traveller
The price is NZ$841
includes taxes & fees
9 Nov - 10 Nov
Apostle Pines #4 @ Apostle Highlands Golf Course
A spacious living room with a wooden ceiling, large windows, a dining area, and a television.

4. Carriage House - Chequamegon Bay, Bayfield

Carriage House - Chequamegon Bay, Bayfield
Bayfield
9.0 out of 10, Wonderful, (16 reviews)
"Great location! Nice and clean."
United States
Janet H.
The price is NZ$841
includes taxes & fees
9 Nov - 10 Nov
Carriage House - Chequamegon Bay, Bayfield
A two-story house with a porch, a garage, and a small attached structure.

5. Carriage @ Hendrickson House

Carriage @ Hendrickson House
Bayfield
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful vacation. This little house was perfect for two people. It had all the amenities that were needed. The best part was it was walking distance to absolutely everything. Prime location. Will definitely be back and staying here again."
United States
Wendy D.
The price is NZ$760
includes taxes & fees
9 Nov - 10 Nov
Carriage @ Hendrickson House
A modern kitchen with a central island, stainless steel appliances, and a bar seating area.

6. Up North Oasis - Families & Dogs in the Bayfield Area

Up North Oasis - Families & Dogs in the Bayfield Area
Washburn
9.8 out of 10, Exceptional, (14 reviews)
"Nice house, and nice location."
United States
ben H.
The price is NZ$578
includes taxes & fees
29 Nov - 30 Nov
Up North Oasis - Families & Dogs in the Bayfield Area
A cozy living room with a sofa, a coffee table, a fireplace, and a fan.

7. 3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Washburn
8.8 out of 10, Excellent, (45 reviews)
"Great location"
United States
vicki A
The price is NZ$772
includes taxes & fees
9 Nov - 10 Nov
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
A modern kitchen with a central island, wooden stools, a stainless steel refrigerator, and a ceiling fan.

8. 2BR Lake Superior Stay | Hot Tub + Walk Downtown

2BR Lake Superior Stay | Hot Tub + Walk Downtown
Ashland
The price is NZ$750
includes taxes & fees
19 Nov - 20 Nov
2BR Lake Superior Stay | Hot Tub + Walk Downtown
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madeline Island Hotel Reviews

The Washburn Inn - On the Lake

The Washburn Inn - On the Lake

10/10 Excellent
"I love staying here! The staff are warm and welcoming, as well as so helpful. The rooms are clean, the location is amazing, and it is a true gem!"
Chloe 3-night trip
Posted 3 days ago
The Washburn Inn - On the Lake

Find out more about Madeline Island

Madeline Island Holiday Homes information

Number of reviews
226
Accommodation
96 Holiday Homes
Lowest Price
NZ$578
Highest Price
NZ$1,026

Explore a world of travel with Expedia