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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Madeline Island vacation rentals

A covered porch with a blue railing, a door labeled "Annex 1", and two chairs.

1. 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
$249 nightly
The price is $265
Oct 21 - Oct 22
Total with taxes and fees
Annex No. 1 DePerrys | On Lake Superior Shoreline
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.
$407 nightly
The price is $460
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.

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
$543 nightly
The price is $608
Oct 25 - Oct 26
Total with taxes and fees
Lake Shore Home with private dock and large deck--1 mile from Bayfield
A wooden deck with a wicker lounge chair and a table, overlooking a forest.

4. 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.
$386 nightly
The price is $435
Nov 1 - Nov 2
Total with taxes and fees
Woodland Chalet @ Brickyard Creek, Bayfield
A sandy beach with a large tree and dense greenery.

5. Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Main Cottage
Bayfield
10.0 out of 10, Exceptional, (58 reviews)
"Our stay was awesome!"
United States
Ramalakshmi
$349 nightly
The price is $391
Oct 30 - Oct 31
Total with taxes and fees
Bayfield Fruit Loop Retreat - Main Cottage
A gazebo with a snow-covered ground, a bench, and a railing.

6. N WI,Bayfield/PEAK fall color now/Stunning/Apostle Is. access/fireplace/jacuzzi

N WI,Bayfield/PEAK fall color now/Stunning/Apostle Is. access/fireplace/jacuzzi
Bayfield
9.8 out of 10, Exceptional, (264 reviews)
"The jacuzzi tub and the fireplace were the best parts of this condo. The bed is comfortable too (but squeaky—not saying this as a negative, but just mentioning for knowledge lol.) Lisa was accommodating and helpful when necessary. Would stay here again!"
United States
Stephanie
$244 nightly
The price is $273
Oct 21 - Oct 22
Total with taxes and fees
N WI,Bayfield/PEAK fall color now/Stunning/Apostle Is. access/fireplace/jacuzzi
A two-story building with a storefront, a visible entrance, and a clear sky.

7. 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
$407 nightly
The price is $468
Nov 1 - Nov 2
Total with taxes and fees
Downtown Bayfield Lodging in Historic Building
A living room with a fireplace, sofas, a TV, and large windows.

8. 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, (22 reviews)
"Great property…. Very clean woth comfortable beds. Great location!"
United States
Marj J.
$315 nightly
The price is $359
Oct 25 - Oct 26
Total with taxes and fees
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
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, (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
$216 nightly
The price is $248
Nov 1 - Nov 2
Total with taxes and fees
Lower Flat @ Steeple Hill Flats, Bayfield
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

10. 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, (43 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
$288 nightly
The price is $304
Nov 16 - Nov 17
Total with taxes and fees
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

11. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (81 reviews)
"A little older cabin than we thought but quaint. Quiet and clean. I would recommend this"
United States
Brian r
$188 nightly
The price is $199
Oct 25 - Oct 26
Total with taxes and fees
Mission Springs Resort
A spacious living room with a stone fireplace, a large brown sofa, a television, and a ceiling fan.

12. 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
$456 nightly
The price is $514
Nov 1 - Nov 2
Total with taxes and fees
Apostle Pines #4 @ Apostle Highlands Golf Course
A hotel room with a large bed, a sitting area with a view, and a bathtub.

13. 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.
$493 nightly
The price is $567
Nov 1 - Nov 2
Total with taxes and fees
Main @ Hendrickson House
A spacious living room with a wooden ceiling, large windows, a dining area, and a television.

14. 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.
$456 nightly
The price is $514
Nov 1 - Nov 2
Total with taxes and fees
Carriage House - Chequamegon Bay, Bayfield
A cabin with a wooden deck and a snow-covered roof, surrounded by snow-laden trees.

15. 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.
$654 nightly
The price is $732
Oct 30 - Oct 31
Total with taxes and fees
Bayfield Fruit Loop Retreat -2 Cottages
A bedroom with two beds, a ceiling fan, a wall-mounted clock, and a bathroom visible through an open door.

16. 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.
$256 nightly
The price is $289
Nov 1 - Nov 2
Total with taxes and fees
Brookside Hide-A-Way #2, Port Superior, Bayfield
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.
$259 nightly
The price is $273
Nov 1 - Nov 2
Total with taxes and fees
The Copper Squirrel is a secluded full log cabin on 10 acres.
A bedroom with a large window, a bed with a white polka dot bedspread, and a view of a grassy yard and trees.

18. 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.
$216 nightly
The price is $242
Oct 27 - Oct 28
Total with taxes and fees
PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
A two-story house with a balcony, large windows, and a covered porch area.

19. 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.
$260 nightly
The price is $298
Nov 1 - Nov 2
Total with taxes and fees
Upper Flat @ Steeple Hill Flats, Bayfield
A single bed with a green blanket, a wooden nightstand with a lamp, and a window with blinds.

20. 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.
$407 nightly
The price is $468
Nov 1 - Nov 2
Total with taxes and fees
Carriage @ Hendrickson House
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
"Solid hotel that’s frequented by a TON of travelers and it’s kept very clean. Breakfast was great every day, food stocked right up until the end. Super helpful and nice staff, highly recommend!!"
TJ 3-night trip
Posted 4 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, 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 $199 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.

Explore a world of travel with Expedia