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

Madeline Island Vacation Rentals

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Check prices for these dates

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

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.
$268 nightly
The price is $300
Oct 8 - Oct 9
Total with taxes and fees
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
$234 nightly
The price is $249
Oct 19 - Oct 20
Total with taxes and fees
Annex No. 1 DePerrys | On Lake Superior Shoreline
A wooden deck with a wicker lounge chair and a table, overlooking a forest.

3. Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield
Bayfield
9.8 out of 10, Exceptional, (67 reviews)
"Host was great and very responsive to questions about check in and once we arrived."
United States
Alex D.
$351 nightly
The price is $396
Nov 1 - Nov 2
Total with taxes and fees
Woodland Chalet @ Brickyard Creek, Bayfield
A gazebo with a snow-covered ground, a bench, and a railing.

4. 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)
"Wonderful place to stay. Lisa is so responsive and truly wants to make sure your needs are met."
United States
Karen W.
$199 nightly
The price is $223
Oct 7 - Oct 8
Total with taxes and fees
Applefest Bayfield available this w/e @discount, near town/fireplace/jacuzzi
A cozy living room with a fireplace, leather sofa, and large windows offering a forest view.

5. 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.
$384 nightly
The price is $433
Nov 1 - Nov 2
Total with taxes and fees
Northwoods Chalet @ Brickyard Creek, 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.

6. 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
$543 nightly
The price is $608
Oct 18 - Oct 19
Total with taxes and fees
Lake Shore Home with private dock and large deck--1 mile from Bayfield
A room with a table and chairs, large windows, and a view of a building and water.

7. 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
$198 nightly
The price is $228
Nov 1 - Nov 2
Total with taxes and fees
Lower Flat @ Steeple Hill Flats, 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
$330 nightly
The price is $369
Oct 30 - Oct 31
Total with taxes and fees
Bayfield Fruit Loop Retreat - Main Cottage
A living room with a fireplace, sofas, a TV, and large windows.

9. 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.
$315 nightly
The price is $359
Oct 8 - Oct 9
Total with taxes and fees
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
A bedroom with a bed, a bedside table, a lamp, and a window with blinds.

10. 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.
$253 nightly
The price is $289
Oct 7 - Oct 8
Total with taxes and fees
Lake Side Room at The Copper Trout.
A two-story building with a storefront, a visible entrance, and a clear sky.

11. Downtown Bayfield Lodging in Historic Building

Downtown Bayfield Lodging in Historic Building
Bayfield
9.6 out of 10, Exceptional, (4 reviews)
"We had an amazing stay! The unit was nice, clean, and modern, with a fantastic location. We loved being able to leave the car parked most days and enjoy most everything Bayfield has to offer within walking distance. We especially enjoyed sitting on the balcony while listening to the Thursday concert in the park or simply watching the ferries go by. Communication with the host was prompt, clear, and easy. We highly recommend this place and would definitely stay here again!"
United States
Dave S.
$396 nightly
The price is $455
Nov 2 - Nov 3
Total with taxes and fees
Downtown Bayfield Lodging in Historic Building
A dining area with a table, chairs, and a large window with a view of a green landscape.

12. 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)
$237 nightly
The price is $265
Oct 7 - Oct 8
Total with taxes and fees
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.

13. 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.
$207 nightly
The price is $234
Nov 1 - Nov 2
Total with taxes and fees
Brookside Hide-A-Way #2, Port Superior, Bayfield
Stunning sunrise & sunset views

14. 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.
$332 nightly
The price is $381
Oct 12 - Oct 13
Total with taxes and fees
Outer Island Apartment @ The Copper Crown
A hotel room with a large bed, a sitting area with a view, and a bathtub.

15. 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.
$468 nightly
The price is $537
Nov 1 - Nov 2
Total with taxes and fees
Main @ Hendrickson House
A spacious living room with a stone fireplace, a large brown sofa, a television, and a ceiling fan.

16. 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.
$433 nightly
The price is $489
Nov 1 - Nov 2
Total with taxes and fees
Apostle Pines #4 @ Apostle Highlands Golf Course
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

17. 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
$332 nightly
The price is $350
Oct 14 - Oct 15
Total with taxes and fees
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
A spacious living room with a wooden ceiling, large windows, a dining area, and a television.

18. 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.
$433 nightly
The price is $489
Nov 1 - Nov 2
Total with taxes and fees
Carriage House - Chequamegon Bay, Bayfield
A beach with a wooden barrier and calm water reflecting sunlight.

19. 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.
$260 nightly
The price is $274
Nov 1 - Nov 2
Total with taxes and fees
The Copper Squirrel is a secluded full log cabin on 10 acres.
A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

20. 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
$187 nightly
The price is $197
Oct 14 - Oct 15
Total with taxes and fees
Mission Springs Resort
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
"Coffee was high-grade; room was fine; safe, small-town feel. Friendly staff. Only issue was the safe. There is a $2 fee for using the safe per day. When you pay $200 or more per night for a room, such fees for an item that always "free" elsewhere just kind of rubs me the wrong way."
David 2-night trip
Posted 2 hours ago
Cobblestone Inn & Suites - 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, 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 $197 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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