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

Madeline Island Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Madeline Island vacation rentals

A covered patio area with a table and chairs, a doormat, and a small garden area.

1. Cozy 1-bedroom condo located on the lake close to downtown.

Cozy 1-bedroom condo located on the lake close to downtown.
La Pointe
$187 nightly
The price is $212
Nov 16 - Nov 17
Total with taxes and fees
Cozy 1-bedroom condo located on the lake close to downtown.
A compact living space with a kitchenette, a television, a ceiling fan, and a wooden cabinet.

2. Bayfield studio, NEW listing/freshly remodeled, Apostle Islands, charming/quaint

Bayfield studio, NEW listing/freshly remodeled, Apostle Islands, charming/quaint
Bayfield
10.0 out of 10, Exceptional, (2 reviews)
"The condo was very clean and everything you would need was there. Lisa was very responsive to any questions we had, and was very helpful. We would definitely recommend it to others."
United States
Carol
$146 nightly
The price is $163
Nov 16 - Nov 17
Total with taxes and fees
Bayfield studio, NEW listing/freshly remodeled, Apostle Islands, charming/quaint
A beach with clear skies, a sandy shore, a tree, and a dock with boats.

3. 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.
$364 nightly
The price is $411
Nov 16 - Nov 17
Total with taxes and fees
Woodland Chalet @ Brickyard Creek, Bayfield
A wooden cabin interior with large windows, a dining table, and chairs.

4. Northwoods Chalet @ Brickyard Creek, Bayfield

Northwoods Chalet @ Brickyard Creek, Bayfield
Bayfield
10.0 out of 10, Exceptional, (84 reviews)
"Beautiful place!"
United States
Susan S.
$384 nightly
The price is $434
Nov 18 - Nov 19
Total with taxes and fees
Northwoods Chalet @ Brickyard Creek, Bayfield
A room with a table and chairs, large windows, and a view of a building and water.

5. 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
$197 nightly
The price is $226
Nov 16 - Nov 17
Total with taxes and fees
Lower Flat @ Steeple Hill Flats, Bayfield
A hotel room with a bed, a desk, a chair, a TV, and a window with a view of trees and water.

6. 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.
$197 nightly
The price is $221
Nov 16 - Nov 17
Total with taxes and fees
PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
A room with a sofa, a lamp, and a view of a balcony with a railing.

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, (24 reviews)
"Location and the host are incredible!"
United States
Michelle N.
$325 nightly
The price is $371
Nov 17 - Nov 18
Total with taxes and fees
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
A wooden dock leading to a cabin surrounded by dense forest and a river.

8. 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
$492 nightly
The price is $551
Nov 21 - Nov 22
Total with taxes and fees
Lake Shore Home with private dock and large deck--1 mile from Bayfield
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

9. 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, (46 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
$243 nightly
The price is $256
Nov 16 - Nov 17
Total with taxes and fees
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
A paved path along a lakeside park with a playground and a building in the background.

10. 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
$162 nightly
The price is $177
Nov 23 - Nov 24
Total with taxes and fees
South Apartment on Main Street
A waterfront property with a covered patio, a brick building, and a view of the sea.

11. 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
$369 nightly
The price is $425
Nov 16 - Nov 17
Total with taxes and fees
Downtown Bayfield Lodging in Historic Building
A covered porch with a wooden ceiling, a wooden door with glass panels, and a table with chairs.

12. 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.
$464 nightly
The price is $534
Nov 16 - Nov 17
Total with taxes and fees
Main @ Hendrickson House
A beach with a wooden barrier and calm water reflecting sunlight.

13. 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, (48 reviews)
"Great place to relax and close enough to Bayfield, a fun and charming seaport."
United States
Tad S.
$235 nightly
The price is $248
Nov 19 - Nov 20
Total with taxes and fees
The Copper Squirrel is a secluded full log cabin on 10 acres.
A kitchen with a microwave, stove, and wooden cabinets. There's a dining table with chairs and a framed artwork above it.

14. 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.
$233 nightly
The price is $263
Nov 16 - Nov 17
Total with taxes and fees
Brookside Hide-A-Way #2, Port Superior, Bayfield
A wooden deck with a railing, overlooking a pond and a grassy area with trees.

15. 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 traveler
$413 nightly
The price is $466
Nov 16 - Nov 17
Total with taxes and fees
Apostle Pines #4 @ Apostle Highlands Golf Course
An outdoor dining area with a wooden table set for four, surrounded by wicker chairs.

16. 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.
$413 nightly
The price is $466
Nov 16 - Nov 17
Total with taxes and fees
Carriage House - Chequamegon Bay, Bayfield
A balcony with a view of a church, a house, and a body of water.

17. 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.
$238 nightly
The price is $273
Nov 16 - Nov 17
Total with taxes and fees
Upper Flat @ Steeple Hill Flats, Bayfield
A beach with a sandy shore, trees, and a body of water.

18. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (82 reviews)
"Clean room, great locations"
United States
Van
$213 nightly
The price is $225
Nov 16 - Nov 17
Total with taxes and fees
Mission Springs Resort
A two-story house with a porch, a garage, and a small attached structure.

19. 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.
$384 nightly
The price is $442
Nov 16 - Nov 17
Total with taxes and fees
Carriage @ Hendrickson House
A dining table with food, a dog, and a chair on a porch.

20. 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.
$291 nightly
The price is $326
Nov 29 - Nov 30
Total with taxes and fees
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.
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Top Madeline Island Hotel Reviews

Blue Wave Inn

Blue Wave Inn

10/10 Excellent
"Very clean and comfortable! Nice to have a coffee/lunch spot downstairs"
Jess 1-night trip
Posted 2 days ago
Blue Wave Inn

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Madeline Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $163 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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