Madeline Island Vacation Rentals from ￥26,086: Search Short-Term Rentals

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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

La Pointe

Anne R.

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

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

Bayfield

Kabao

￥39,180 total

includes taxes & fees

Oct 19 - Oct 20

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

3. Woodland Chalet @ Brickyard Creek, Bayfield

Bayfield

Alex D.

￥62,560 total

includes taxes & fees

Nov 4 - Nov 5

A gazebo with a snow-covered ground, a bench, and a railing.

4. Apostle Islands gateway/next to Marinas/fireplace/jacuzzi/end unit w/ 4 windows

Bayfield

Karen W.

A cozy living room with a fireplace, leather sofa, and large windows offering a forest view.

5. Northwoods Chalet @ Brickyard Creek, Bayfield

Bayfield

Susan S.

￥68,396 total

includes taxes & fees

Nov 1 - Nov 2

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

Bayfield

Brian

￥96,030 total

includes taxes & fees

Oct 18 - Oct 19

A room with a table and chairs, large windows, and a view of a building and water.

7. Lower Flat @ Steeple Hill Flats, Bayfield

Bayfield

Lori

￥35,922 total

includes taxes & fees

Nov 1 - Nov 2

A sandy beach with a large tree and dense greenery.

8. Bayfield Fruit Loop Retreat - Main Cottage

Bayfield

￥57,408 total

includes taxes & fees

Oct 30 - Oct 31

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

Bayfield

Marj J.

￥56,703 total

includes taxes & fees

Oct 20 - Oct 21

A bedroom with a bed, a bedside table, a lamp, and a window with blinds.

10. Lake Side Room at The Copper Trout.

Bayfield

Cee R.

￥50,943 total

includes taxes & fees

Nov 1 - Nov 2

A two-story building with a storefront, a visible entrance, and a clear sky.

11. Downtown Bayfield Lodging in Historic Building

Bayfield

"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!"

Dave S.

￥71,828 total

includes taxes & fees

Nov 2 - Nov 3

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

Bayfield

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

Bayfield

Don L.

￥36,940 total

includes taxes & fees

Nov 1 - Nov 2

14. Outer Island Apartment @ The Copper Crown

Bayfield

Rickandheather H.

￥60,220 total

includes taxes & fees

Oct 12 - Oct 13

A hotel room with a large bed, a sitting area with a view, and a bathtub.

15. Main @ Hendrickson House

Bayfield

Aaron G.

￥84,845 total

includes taxes & fees

Nov 5 - Nov 6

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

Bayfield

Mark H.

￥77,146 total

includes taxes & fees

Nov 1 - Nov 2

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!

Bayfield

elizabeth

￥55,306 total

includes taxes & fees

Oct 14 - Oct 15

A spacious living room with a wooden ceiling, large windows, a dining area, and a television.

18. Carriage House - Chequamegon Bay, Bayfield

Bayfield

￥77,146 total

includes taxes & fees

Nov 1 - Nov 2

A beach with a wooden barrier and calm water reflecting sunlight.

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

Bayfield

Tad S.

A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

20. Mission Springs Resort

Ashland

Brian r

￥26,086 total

includes taxes & fees

Oct 21 - Oct 22

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Top Madeline Island Hotel Reviews

Hotel Chequamegon, BW Signature Collection

8/10 Good

"We had a suite with a kitchen that was way outdated and had very little kitchen items. The full size frig was nice. The stove top was rusty. The room was clean and the bed was comfortable. I'd recommend removing the kitchen, put in a wet bar and add a nice sitting area."

The Washburn Inn - On the Lake

10/10 Excellent

"Pros: Staff was friendly. Place was expectedly though not exceptionally clean. AC was nice. Shower was nice. Rooms were a good size. No drinking water (except bottled available) but did have coffee and hot water available. Microwave available. Ice machine available. There are places to sit and watch the sunrise/sunset on the lake. Restaurant nearby when open. Cons: No elevator to second floor. Our room did not have a lake view, but rather of the parking lot, though we didn't mind as we didn't spend a lot of time there. Beds were not the most comfortable. AC would not keep a consistent temp so we were often too warm or too cold."

Private Beach and Endless Water

8/10 Good

"The place was fine. It did the trick and we had a great time. However, I feel we overpaid to be honest. The endless beach was not endless. In fact, it was quite small. Maybe 50-80ft. The beach access was also across the street and down the road. Based on the description and pictures, I was lead to believe this was a waterfront property. It is not. The cleanliness of the trailer itself left something to be desired. It was by no means bad, but dusty, a bit buggy, lots of cobwebs, and there was a load of wet laundry in the washing machine when we got there. Also, the vacuum was left in the middle of the main room which we thought was odd. Again, we very much enjoyed our stay and the place did what it needed to do. But it was expensive compared to other options on the island, and it’s not waterfront like we had hoped which was quite disappointing."

Find out more about Madeline Island

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Madeline Island Vacation Rentals

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Check prices for these dates

Our top choices for Madeline Island vacation rentals

1. Suite One at La Pointe Lodging

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

3. Woodland Chalet @ Brickyard Creek, Bayfield

4. Apostle Islands gateway/next to Marinas/fireplace/jacuzzi/end unit w/ 4 windows

5. Northwoods Chalet @ Brickyard Creek, Bayfield

6. Lake Shore Home with private dock and large deck--1 mile from Bayfield

7. Lower Flat @ Steeple Hill Flats, Bayfield

8. Bayfield Fruit Loop Retreat - Main Cottage

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

10. Lake Side Room at The Copper Trout.

11. Downtown Bayfield Lodging in Historic Building

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

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

14. Outer Island Apartment @ The Copper Crown

15. Main @ Hendrickson House

16. Apostle Pines #4 @ Apostle Highlands Golf Course

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

18. Carriage House - Chequamegon Bay, Bayfield

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

20. Mission Springs Resort

Find vacation rentals that suit your style

Top Madeline Island Hotel Reviews

Hotel Chequamegon, BW Signature Collection

Find out more about Madeline Island

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