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

Holiday Homes in Madeline Island

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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, (122 reviews)
"Great property! wonderful rejuvenation time for myself and my family"
United States
Brian
The price is AU$844
includes taxes & fees
18 Oct - 19 Oct
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, (2 reviews)
"Very nice and spotless. Also a great location within a couple blocks of almost everything. We’ll be back."
United States
Aaron G.
The price is AU$749
includes taxes & fees
1 Nov - 2 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, (21 reviews)
"Outstanding property in all ways, highly recommended."
United States
Mark H.
The price is AU$683
includes taxes & fees
1 Nov - 2 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 AU$683
includes taxes & fees
1 Nov - 2 Nov
Carriage House - Chequamegon Bay, Bayfield
A single bed with a green blanket, a wooden nightstand with a lamp, and a window with blinds.

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 AU$617
includes taxes & fees
1 Nov - 2 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, (12 reviews)
"We had a lovely stay and the accommodations were just what we needed. We are planning to stay here again. "
United States
Joan Q.
The price is AU$496
includes taxes & fees
1 Nov - 2 Nov
Up North Oasis - Families & Dogs in the Bayfield Area
A backyard with a wooden deck, stepping stones, raised garden beds with flowers, and a chair.

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, (43 reviews)
"We had a great time! Beautiful home with easy access to all the South Shore has to offer. "
United States
Anastasia Hopkins F.
The price is AU$637
includes taxes & fees
11 Oct - 12 Oct
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
A dining area with a wooden table and chairs, a hanging light fixture, a fireplace, and a painting on the wall.

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

2BR Lake Superior Stay | Hot Tub + Walk Downtown
Ashland
The price is AU$656
includes taxes & fees
8 Nov - 9 Nov
2BR Lake Superior Stay | Hot Tub + Walk Downtown
A brick building with a door and potted plants in front.

9. Historic Main St w/ Lake View | The Flatwater Loft

Historic Main St w/ Lake View | The Flatwater Loft
Ashland
10.0 out of 10, Exceptional, (3 reviews)
"Awesome location, great communication with host,Flat was newly decorated in 40’s deco. Loved loved the charm of the flat."
United States
Judy D.
The price is AU$781
includes taxes & fees
28 Oct - 29 Oct
Historic Main St w/ Lake View | The Flatwater Loft
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

Cobblestone Inn & Suites - Ashland

Cobblestone Inn & Suites - Ashland

10/10 Excellent
"Better breakfast than other hotels. Coffee 24/7. Beautiful view of the lake."
Linda 3-night trip
Posted 4 hours ago
Cobblestone Inn & Suites - Ashland

Find out more about Madeline Island

Madeline Island Holiday Homes information

Number of reviews
209
Accommodation
96 Holiday Homes
Lowest Price
AU$496
Highest Price
AU$844