Madeline Island Holiday Rentals from NZ$327: Search Short-Term Rentals

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Our top choices for Madeline Island holiday 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

Bayfield

Kabao

includes taxes & fees

19 Oct - 20 Oct

A wooden cabin with a porch and steps, surrounded by trees.

2. Woodland Chalet @ Brickyard Creek, Bayfield

Bayfield

Reed C.

includes taxes & fees

8 Nov - 9 Nov

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

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

Bayfield

Karen W.

includes taxes & fees

18 Oct - 19 Oct

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

4. Northwoods Chalet @ Brickyard Creek, Bayfield

Bayfield

Susan S.

includes taxes & fees

5 Nov - 6 Nov

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

5. Lower Flat @ Steeple Hill Flats, Bayfield

Bayfield

Lori

includes taxes & fees

2 Nov - 3 Nov

A living room with a fireplace, sofas, a TV, and large windows.

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

Bayfield

Marj J.

includes taxes & fees

19 Oct - 20 Oct

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

7. Downtown Bayfield Lodging in Historic Building

Bayfield

"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."

Susan

includes taxes & fees

2 Nov - 3 Nov

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.

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

Bayfield

Brian

includes taxes & fees

18 Oct - 19 Oct

A sandy beach with a large tree and dense greenery.

9. Bayfield Fruit Loop Retreat - Main Cottage

Bayfield

Ramalakshmi

includes taxes & fees

30 Oct - 31 Oct

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

10. Main @ Hendrickson House

Bayfield

Aaron G.

includes taxes & fees

1 Nov - 2 Nov

A bedroom with two beds, a ceiling fan, a wall-mounted clock, and a bathroom visible through an open door.

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

Bayfield

Don L.

includes taxes & fees

2 Nov - 3 Nov

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

Bayfield

Mark H.

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a large window, a bed with a white polka dot bedspread, and a view of a grassy yard and trees.

13. PORT 1 bedroom studio with AC just 2.5 miles from Bayfield

Bayfield

scott d.

includes taxes & fees

27 Oct - 28 Oct

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

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

Bayfield

Tad S.

includes taxes & fees

1 Nov - 2 Nov

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

15. Carriage House - Chequamegon Bay, Bayfield

Bayfield

Janet H.

includes taxes & fees

1 Nov - 2 Nov

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

16. Mission Springs Resort

Ashland

Brian r

includes taxes & fees

21 Oct - 22 Oct

A two-story house with a balcony, large windows, and a covered porch area.

17. Upper Flat @ Steeple Hill Flats, Bayfield

Bayfield

Josh F.

includes taxes & fees

16 Nov - 17 Nov

A single bed with a green blanket, a wooden nightstand with a lamp, and a window with blinds.

18. Carriage @ Hendrickson House

Bayfield

Wendy D.

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a wooden table and bar stools, a ceiling fan, and pendant lights.

19. South Apartment on Main Street

Ashland

Mark

includes taxes & fees

9 Nov - 10 Nov

A cabin with a wooden deck and a snow-covered roof, surrounded by snow-laden trees.

20. Bayfield Fruit Loop Retreat -2 Cottages

Bayfield

Tami N.

includes taxes & fees

30 Oct - 31 Oct

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Top Madeline Island Hotel Reviews

Lakeside Motel

10/10 Excellent

"Very clean nice room. Great location"

Hotel Chequamegon, BW Signature Collection

8/10 Good

"It's an old, restored building. The architecture is beautiful, but the rooms are definitely dated. Old, noisy air conditioners, etc. The restaurant was very good, however that was the only place to eat within walking distance other than fast food. The breakfast staff apparently didn't show up on our last day, so all that they had was coffee and toast. While it was nice to say we've stayed there, we won't stay there again."

Seagull Bay Motel

10/10 Excellent

"Beautiful location within easy 5-10 minute walking distance to downtown Bayfield shops, restaurants, and the ferry to Madeline Island. We were there for peak fall leaves color. The view of the lake, the island, the small marina, the trees, and the sunrise from the cozy furniture on the deck outside our door was amazing. It is a motel, so there is the potential for noise from the vehicles that park outside the rooms, but it was a non-issue. Our stay was peaceful, pleasant, and perfect."

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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Madeline Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Madeline Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Madeline Island. Seeing all the best attractions is bound to make you fall in love with Madeline Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Madeline Island short-term rentals, that won’t be hard to do.

Madeline Island Holiday Rentals

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Check prices for these dates

Our top choices for Madeline Island holiday rentals

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

2. Woodland Chalet @ Brickyard Creek, Bayfield

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

4. Northwoods Chalet @ Brickyard Creek, Bayfield

5. Lower Flat @ Steeple Hill Flats, Bayfield

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

7. Downtown Bayfield Lodging in Historic Building

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

9. Bayfield Fruit Loop Retreat - Main Cottage

10. Main @ Hendrickson House

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

12. Apostle Pines #4 @ Apostle Highlands Golf Course

13. PORT 1 bedroom studio with AC just 2.5 miles from Bayfield

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

15. Carriage House - Chequamegon Bay, Bayfield

16. Mission Springs Resort

17. Upper Flat @ Steeple Hill Flats, Bayfield

18. Carriage @ Hendrickson House

19. South Apartment on Main Street

20. Bayfield Fruit Loop Retreat -2 Cottages

Find holiday rentals that suit your style

Top Madeline Island Hotel Reviews

Lakeside Motel

Find out more about Madeline Island

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