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

Madeline Island Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Madeline Island holiday rentals

A wooden deck with a wicker lounge chair and a table, overlooking a forest.

1. Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield
Bayfield
9.8 out of 10, Exceptional, (67 reviews)
"Very clean and cozy cabin near Bayfield and Meyers beach"
United States
Reed C.
The price is AU$598
includes taxes & fees
1 Nov - 2 Nov
Woodland Chalet @ Brickyard Creek, Bayfield
A cozy living room with a fireplace, leather sofa, and large windows offering a forest view.

2. Northwoods Chalet @ Brickyard Creek, Bayfield

Northwoods Chalet @ Brickyard Creek, Bayfield
Bayfield
10.0 out of 10, Exceptional, (83 reviews)
"Beautiful place!"
United States
Susan S.
The price is AU$632
includes taxes & fees
1 Nov - 2 Nov
Northwoods Chalet @ Brickyard Creek, Bayfield
A deck with a fire feature, outdoor seating, and string lights.

3. Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Main Cottage
Bayfield
10.0 out of 10, Exceptional, (61 reviews)
"Our stay was awesome!"
United States
Ramalakshmi
Bayfield Fruit Loop Retreat - Main Cottage
A room with a table and chairs, large windows, and a view of a building and water.

4. Lower Flat @ Steeple Hill Flats, Bayfield

Lower Flat @ Steeple Hill Flats, Bayfield
Bayfield
9.2 out of 10, Wonderful, (26 reviews)
"Nice and cozy with a great view. The outside spaces could use some tidying up and paint, but once inside the place was awesome."
United States
Lori
The price is AU$351
includes taxes & fees
6 Nov - 7 Nov
Lower Flat @ Steeple Hill Flats, Bayfield
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.

5. 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 AU$838
includes taxes & fees
1 Nov - 2 Nov
Lake Shore Home with private dock and large deck--1 mile from Bayfield
A waterfront property with a covered patio, a brick building, and a view of the sea.

6. Downtown Bayfield Lodging in Historic Building

Downtown Bayfield Lodging in Historic Building
Bayfield
9.2 out of 10, Wonderful, (5 reviews)
"Loved the rooms! Enjoyed the views of the lake and the quaint downtown area. It was a very quiet and enjoyable stay. I gave it 4 stars only because the sofa was so hard and uncomfortable. We stayed in 2 nights to watch the Brewers play (YAY!) but it was very difficult to get comfortable on the sofa and no amount of throw pillows could change that. That being said, the bed was a dream and the kitchen well appointed. Would I stay there again? Maybe if the sofa was swapped out."
United States
Susan
The price is AU$643
includes taxes & fees
1 Nov - 2 Nov
Downtown Bayfield Lodging in Historic Building
A living room with a fireplace, sofas, a TV, and large windows.

7. Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield

Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
Bayfield
10.0 out of 10, Exceptional, (23 reviews)
"Location and the host are incredible!"
United States
Michelle N.
The price is AU$536
includes taxes & fees
12 Nov - 13 Nov
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

8. The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!

The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
Bayfield
10.0 out of 10, Exceptional, (44 reviews)
"Enjoyed our few nights at this lovely home. So many special touches! Really enjoyed the screened in area and lighting fires and having smores around the fire pit."
United States
elizabeth
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
A hotel room with a large bed, a sitting area with a view, and a bathtub.

9. 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$772
includes taxes & fees
12 Nov - 13 Nov
Main @ Hendrickson House
A spacious living room with a stone fireplace, a large brown sofa, a television, and a ceiling fan.

10. 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 AU$705
includes taxes & fees
12 Nov - 13 Nov
Apostle Pines #4 @ Apostle Highlands Golf Course
A bedroom with two beds, a ceiling fan, a wall-mounted clock, and a bathroom visible through an open door.

11. Brookside Hide-A-Way #2, Port Superior, Bayfield

Brookside Hide-A-Way #2, Port Superior, Bayfield
Bayfield
9.8 out of 10, Exceptional, (42 reviews)
"Great place and wonderful rear deck. Wish we had more time to spend there."
United States
Don L.
The price is AU$402
includes taxes & fees
1 Nov - 2 Nov
Brookside Hide-A-Way #2, Port Superior, Bayfield
A bedroom with a large window, a bed with a white polka dot bedspread, and a view of a grassy yard and trees.

12. PORT 1 bedroom studio with AC just 2.5 miles from Bayfield

PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
Bayfield
10.0 out of 10, Exceptional, (1 review)
"Great location, nice view from bedroom. Easy in and out and good communication. Could use darker shades."
United States
scott d.
The price is AU$349
includes taxes & fees
4 Nov - 5 Nov
PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
A spacious living room with a wooden ceiling, large windows, a dining area, and a television.

13. 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$705
includes taxes & fees
12 Nov - 13 Nov
Carriage House - Chequamegon Bay, Bayfield
A two-story house with a balcony, large windows, and a covered porch area.

14. Upper Flat @ Steeple Hill Flats, Bayfield

Upper Flat @ Steeple Hill Flats, Bayfield
Bayfield
8.6 out of 10, Excellent, (18 reviews)
"Great views of Superior and comfortable stay"
United States
Josh F.
The price is AU$426
includes taxes & fees
10 Nov - 11 Nov
Upper Flat @ Steeple Hill Flats, Bayfield
A two-story house with a porch, a garage, and a small attached structure.

15. 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$641
includes taxes & fees
12 Nov - 13 Nov
Carriage @ Hendrickson House
A modern kitchen with a wooden table and bar stools, a ceiling fan, and pendant lights.

16. South Apartment on Main Street

South Apartment on Main Street
Ashland
9.8 out of 10, Exceptional, (25 reviews)
"Very nice accommodations. Close to downtown area with shops and Bayview park. "
United States
Mark
The price is AU$267
includes taxes & fees
9 Nov - 10 Nov
South Apartment on Main Street
A cabin with a wooden deck and a snow-covered roof, surrounded by snow-laden trees.

17. Bayfield Fruit Loop Retreat -2 Cottages

Bayfield Fruit Loop Retreat -2 Cottages
Bayfield
9.8 out of 10, Exceptional, (8 reviews)
"These cottages are the cleanest we have ever stayed in. Great for groups because of the cottage locations. Amenities were absolutely complete and perfect!"
United States
Tami N.
Bayfield Fruit Loop Retreat -2 Cottages
A modern kitchen with a central island, stainless steel appliances, and a bar seating area.

18. 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)
"Great place to stay! Plenty of amenities and Dog friendly. Would definitely stay here again. "
United States
Susan B.
The price is AU$474
includes taxes & fees
29 Nov - 30 Nov
Up North Oasis - Families & Dogs in the Bayfield Area
A modern living room with a blue sofa, wooden dining table, and a view of a parking lot through large windows.

19. North Apartment with Lake Superior Views

North Apartment with Lake Superior Views
Ashland
10.0 out of 10, Exceptional, (46 reviews)
"Great location, clean and comfortable. "
United States
Heather Ann M.
The price is AU$325
includes taxes & fees
8 Nov - 9 Nov
North Apartment with Lake Superior Views
A cozy living room with a sofa, a coffee table, a fireplace, and a fan.

20. 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$631
includes taxes & fees
2 Nov - 3 Nov
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
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

Hotel Chequamegon, BW Signature Collection

Hotel Chequamegon, BW Signature Collection

10/10 Excellent
"Very clean facility, excellent breakfast!"
Connie 2-night trip
Posted 5 hours ago
Hotel Chequamegon, BW Signature Collection

Find out more about Madeline Island

Everything you need to know about Madeline Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Madeline Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madeline Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Madeline Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madeline Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madeline Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madeline Island holiday rentals we have selected for you start as low as AU$319 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Madeline Island rentals

At Expedia, we put the best Madeline Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Madeline Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madeline Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madeline Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.