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

Madeline Island Vacation Rentals

  • 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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Madeline Island vacation rentals

A deck with two Adirondack chairs, a door, and a window.

1. Suite One at La Pointe Lodging

Suite One at La Pointe Lodging
La Pointe
9.8 out of 10, Exceptional, (28 reviews)
"Lovely place!!"
United States
Anne R.
The price is CA $267
CA $443 total
includes taxes & fees
Oct 8 - Oct 9
Suite One at La Pointe Lodging
A covered porch with a blue railing, a door labeled "Annex 1", and two chairs.

2. Annex No. 1 DePerrys | On Lake Superior Shoreline

Annex No. 1 DePerrys | On Lake Superior Shoreline
Bayfield
9.8 out of 10, Exceptional, (48 reviews)
"Cute and cozy little place! Perfect for our anniversary weekend getaway!"
United States
Kabao
The price is CA $221
CA $351 total
includes taxes & fees
Oct 6 - Oct 7
Annex No. 1 DePerrys | On Lake Superior Shoreline
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.

3. 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 CA $427
CA $855 total
includes taxes & fees
Oct 18 - Oct 19
Lake Shore Home with private dock and large deck--1 mile from Bayfield
Exterior

4. The Little Bodin

The Little Bodin
Bayfield
9.8 out of 10, Exceptional, (69 reviews)
"Great central location in downtown Bayfield. Very clean. Perfect for our family of four’s long weekend in Bayfield."
United States
Andrew
The price is CA $307
CA $537 total
includes taxes & fees
Oct 4 - Oct 5
The Little Bodin
A bedroom with a bed, a bedside table, a lamp, and a window with blinds.

5. Lake Side Room at The Copper Trout.

Lake Side Room at The Copper Trout.
Bayfield
9.2 out of 10, Wonderful, (113 reviews)
"Great location."
United States
Cee R.
The price is CA $319
CA $407 total
includes taxes & fees
Oct 4 - Oct 5
Lake Side Room at The Copper Trout.
A gazebo with a snow-covered ground, a bench, and a railing.

6. Applefest Bayfield available this w/e @discount, near town/fireplace/jacuzzi

Applefest Bayfield available this w/e @discount, near town/fireplace/jacuzzi
Bayfield
9.8 out of 10, Exceptional, (261 reviews)
"Very cute condo. Close to the city."
United States
Cindy B.
The price is CA $170
CA $316 total
includes taxes & fees
Oct 7 - Oct 8
Applefest Bayfield available this w/e @discount, near town/fireplace/jacuzzi
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, (20 reviews)
"Great property…. Very clean woth comfortable beds. Great location!"
United States
Marj J.
The price is CA $213
CA $511 total
includes taxes & fees
Oct 8 - Oct 9
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
A sandy beach with a large tree and dense greenery.

8. Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Main Cottage
Bayfield
10.0 out of 10, Exceptional, (57 reviews)
"Our stay was awesome!"
United States
Ramalakshmi
The price is CA $423
CA $543 total
includes taxes & fees
Oct 30 - Oct 31
Bayfield Fruit Loop Retreat - Main Cottage
A room with a table and chairs, large windows, and a view of a building and water.

9. Lower Flat @ Steeple Hill Flats, Bayfield

Lower Flat @ Steeple Hill Flats, Bayfield
Bayfield
9.2 out of 10, Wonderful, (25 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 CA $196
CA $328 total
includes taxes & fees
Nov 1 - Nov 2
Lower Flat @ Steeple Hill Flats, Bayfield
Stunning sunrise & sunset views

10. Outer Island Apartment @ The Copper Crown

Outer Island Apartment @ The Copper Crown
Bayfield
9.8 out of 10, Exceptional, (15 reviews)
"Great location and nice little space to stay near the downtown area."
United States
Rickandheather H.
The price is CA $327
CA $538 total
includes taxes & fees
Oct 12 - Oct 13
Outer Island Apartment @ The Copper Crown
A dining area with a table, chairs, and a large window with a view of a green landscape.

11. Cozy 1-bedroom studio in serene Bayfield with AC

Cozy 1-bedroom studio in serene Bayfield with AC
Bayfield
9.4 out of 10, Exceptional, (8 reviews)
The price is CA $171
CA $382 total
includes taxes & fees
Oct 8 - Oct 9
Cozy 1-bedroom studio in serene Bayfield with AC
A bedroom with two beds, a ceiling fan, a wall-mounted clock, and a bathroom visible through an open door.

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

Brookside Hide-A-Way #2, Port Superior, Bayfield
Bayfield
9.8 out of 10, Exceptional, (41 reviews)
"Great place and wonderful rear deck. Wish we had more time to spend there."
United States
Don L.
The price is CA $188
CA $331 total
includes taxes & fees
Nov 1 - Nov 2
Brookside Hide-A-Way #2, Port Superior, Bayfield
A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

13. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (79 reviews)
"A little older cabin than we thought but quaint. Quiet and clean. I would recommend this"
United States
Brian r
The price is CA $223
CA $235 total
includes taxes & fees
Oct 21 - Oct 22
Mission Springs Resort
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

14. 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, (41 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 price is CA $356
CA $495 total
includes taxes & fees
Oct 14 - Oct 15
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
A bedroom with a bed, bedside table, lamp, and a dresser with a coffee maker.

15. Avenue Side Room at The Copper Trout.

Avenue Side Room at The Copper Trout.
Bayfield
9.6 out of 10, Exceptional, (93 reviews)
"The room was awesome - all that we needed. Right in town so very walkable. We would definitely stay here again when we are in the area."
United States
Brendon
The price is CA $319
CA $407 total
includes taxes & fees
Oct 4 - Oct 5
Avenue Side Room at The Copper Trout.
A cabin with a wooden deck and a snow-covered roof, surrounded by snow-laden trees.

16. 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.
The price is CA $820
CA $1,034 total
includes taxes & fees
Oct 5 - Oct 6
Bayfield Fruit Loop Retreat -2 Cottages
A beach with a wooden barrier and calm water reflecting sunlight.

17. The Copper Squirrel is a secluded full log cabin on 10 acres.

The Copper Squirrel is a secluded full log cabin on 10 acres.
Bayfield
10.0 out of 10, Exceptional, (45 reviews)
"Great place to relax and close enough to Bayfield, a fun and charming seaport."
United States
Tad S.
The price is CA $269
CA $390 total
includes taxes & fees
Nov 1 - Nov 2
The Copper Squirrel is a secluded full log cabin on 10 acres.
A two-story house with a balcony, large windows, and a covered porch area.

18. Upper Flat @ Steeple Hill Flats, Bayfield

Upper Flat @ Steeple Hill Flats, Bayfield
Bayfield
8.8 out of 10, Excellent, (15 reviews)
"Great views of Superior and comfortable stay"
United States
Josh F.
The price is CA $221
CA $399 total
includes taxes & fees
Nov 1 - Nov 2
Upper Flat @ Steeple Hill Flats, Bayfield
A modern kitchen with a wooden table and bar stools, a ceiling fan, and pendant lights.

19. South Apartment on Main Street

South Apartment on Main Street
Ashland
9.8 out of 10, Exceptional, (24 reviews)
"Very nice accommodations. Close to downtown area with shops and Bayview park. "
United States
Mark
The price is CA $178
CA $310 total
includes taxes & fees
Oct 5 - Oct 6
South Apartment on Main Street
A modern kitchen with a central island, stainless steel appliances, and a bar seating area.

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

Up North Oasis - Families & Dogs in the Bayfield Area
Washburn
10.0 out of 10, Exceptional, (11 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 CA $221
CA $503 total
includes taxes & fees
Nov 1 - Nov 2
Up North Oasis - Families & Dogs in the Bayfield Area
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

Super 8 by Wyndham Ashland

Super 8 by Wyndham Ashland

10/10 Excellent
"It's an older Hotel, but it's still very nice for the price and the area. The room was quite, the beds are nice. Breakfast was very nice, There was a wide veriety to choose from."
Bonni 1-night trip
Posted 3 hours ago
Super 8 by Wyndham Ashland

Find out more about Madeline Island

Everything you need to know about Madeline Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madeline Island vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Madeline Island vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madeline Island vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madeline Island vacation rentals we have selected for you start as low as CA $235 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Madeline Island rentals

At Expedia, we put the best Madeline Island vacation 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 vacation.

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. 

Explore a world of travel with Expedia