Madeline Island Holiday Rentals, Wisconsin: Private House Rentals

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

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Go beyond your typical stay in Madeline Island

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Our top choices for Madeline Island hotels

A rooftop terrace with wicker furniture, a view of the sea, and a brick building in the background.

A sauna room with wooden benches and a large window.

A bar area with a leather couch, wicker chairs, and a bar counter.

A dining area with a wooden ceiling, wicker furniture, and a central floral arrangement.

1. St. James Social

Bayfield

Michelle

฿11,895

฿13,560 total

includes taxes & fees

21 Oct - 22 Oct

A large white building with a green roof, a covered entrance, and a view of the water.

A traditional living room with leather furniture, a fireplace, and a bookshelf.

A grand lobby with a central staircase, wooden columns, and a chandelier.

A restaurant with wooden tables and chairs, a kitchen area, and a clock on the wall.

2. Hotel Chequamegon, BW Signature Collection

Ashland

DOROTHY

฿4,292

฿4,807 total

includes taxes & fees

1 Nov - 2 Nov

A modern bedroom with a wooden bed, a TV mounted on the wall, and a seating area with a sofa and chairs.

A modern living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall.

A row of white cabins with wooden railings and a grassy lawn.

A wooden deck with a hanging chair, two white chairs, and a potted plant.

3. Seagull Bay Motel

Bayfield

Melissa

฿5,722

฿6,523 total

includes taxes & fees

7 Oct - 8 Oct

A marina filled with various boats at sunset.

An aerial view of a hotel with a parking lot, a marina with boats, and a body of water in the background.

A grassy outdoor area with white chairs arranged in rows, a small arbor, and a bench.

A row of colorful Adirondack chairs and tables by a lakeside, with a clear view of the water and distant shoreline.

4. The Washburn Inn - On the Lake

Washburn

Michael

฿3,247

฿3,636 total

includes taxes & fees

19 Oct - 20 Oct

A room with two patterned armchairs, a small table with a lamp, and a mirror on the wall.

A bedroom with a large bed, two bedside lamps, a chair, and a window with curtains.

A living room with a green sofa, a brown leather armchair, a wooden coffee table, and a window with a view of trees.

A spacious living room with a wooden staircase, a green sofa, and a lamp on a side table.

5. Pinehurst Inn - Luxury Bayfield Hotel

Bayfield

Carrie

฿5,330

฿5,969 total

includes taxes & fees

2 Nov - 3 Nov

A modern living room with a stone wall, a fireplace, leather sofas, and glass coffee tables.

A hotel room with a large bed, a sofa, a desk, and a framed picture on the wall.

A Cobblestone Inn & Suites building with a brick facade, a covered entrance, and a parking lot.

A modern restaurant with a bar area, seating, and a large window offering a view of the street.

6. Cobblestone Inn & Suites - Ashland

Ashland

Adrian

฿4,802

฿5,379 total

includes taxes & fees

21 Oct - 22 Oct

A multi-level indoor pool area with stone walls and wooden railings.

A wooden deck with a table and chairs overlooking a calm body of water.

A room with a round table, chairs, a flat-screen TV, and large windows offering a view of a body of water and trees.

A modern kitchen with dark wood cabinets, a large stove, and a microwave.

7. Quality Inn Ashland - Lake Superior

Ashland

Marie

฿4,355

฿4,878 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio with a table and chairs, overlooking a body of water at sunset.

An indoor swimming pool with a wooden ceiling, slides, and poolside chairs.

A dining area with multiple tables and chairs, large windows offering a view of the sea, and a carpeted floor.

A beach with turquoise chairs and a pile of logs.

8. AmericInn by Wyndham Ashland

Ashland

Jonathan

฿3,594

฿4,026 total

includes taxes & fees

1 Nov - 2 Nov

A modern building with a unique architectural design, situated on a rocky shoreline with a body of water in the foreground.

A wooden staircase leading to a bright room with large windows and a view of a parking lot.

A restaurant with a large round window overlooking the sea, wooden tables and chairs, and a staircase leading to an upper level.

A modern building with large windows and outdoor seating.

9. Blue Wave Inn

Ashland

Dawn

฿2,990

฿3,349 total

includes taxes & fees

1 Nov - 2 Nov

A modern bedroom with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.

A compact kitchenette with a microwave, coffee maker, sink, and dishwasher.

A living room with a black leather sofa, a wooden chair, a small table with two stools, a floor lamp, and a large mirror.

A motel with a simple, single-story structure, a parking lot, and a signboard.

10. Lakeside Motel

Ashland

Patti

฿2,517

฿2,819 total

includes taxes & fees

19 Oct - 20 Oct

A framed photograph of a turbulent sea on a wall, a bedside lamp, and a pillow on a bed.

A living room with a sofa, a coffee table, a TV, and a cabinet.

A motel with a brick facade, a covered entrance, and a row of chairs outside.

A pool area with wooden walls, a pool, and several chairs.

11. Super 8 by Wyndham Ashland

Ashland

Bonni

฿3,896

฿4,363 total

includes taxes & fees

31 Oct - 1 Nov

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

A two-story house with a wooden deck and a staircase leading to the entrance.

A dining area with a white table, chairs, and a chandelier. There is a sign on the wall that reads "Welcome to THE LAKE HOUSE."

A beach with a sandy shore, trees, and a body of water.

12. Mission Springs Resort

Ashland

Brian r

฿5,255

฿5,544 total

includes taxes & fees

21 Oct - 22 Oct

A room with a wooden deck visible through a glass door, a wooden table, and two black chairs.

A modern kitchen with a white countertop, black bar stools, a wooden ceiling, and a window with a towel rack.

A room with a wooden floor, a round table with chairs, a potted plant, and a bed with a white headboard.

A living room with a sofa, wooden flooring, a chandelier, and a large window with a view.

13. Outbounder

Bayfield

Helen

฿5,537

฿6,313 total

includes taxes & fees

7 Oct - 8 Oct

A bar with a view of a lake and boats, large windows, and hanging light fixtures.

Outdoor wicker lounge chairs and a table in front of a building with red and blue exterior walls and multiple windows.

A spacious lobby with a stone fireplace, comfortable seating, and a patterned floor.

A waterfront hotel with multiple buildings, a dock, and a speedboat on the water.

14. Legendary Waters Resort & Casino

Bayfield

Michael

A cozy loft-style room with a dining area, a kitchen, and a staircase.

A room with a bed, a sofa, a small table, a chair, a TV, and a window with curtains.

A compact kitchen with a sink, a coffee maker, a microwave, and a dishwasher.

A brown leather sofa with a striped pillow and a tall, textured floor lamp.

15. The Mill House

Bayfield

Christopher

฿8,180

฿9,325 total

includes taxes & fees

20 Oct - 21 Oct

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Stay near popular Madeline Island attractions

Big Bay State Park

9.2/10 (9 reviews)

Dramatic sandstone bluffs meet pristine Lake Superior beaches at this Madeline Island sanctuary. Explore seven miles of forest trails or paddle the protected lagoon for an intimate wilderness experience.

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Madeline Island Museum

9.0/10 (17 reviews)

Housed in the 1835 American Fur Company Building, this museum chronicles Madeline Island's Native American and fur trade history. Explore maritime artefacts while staff illuminate the island's cultural significance.

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Learn more about Madeline Island

Head to sights like Big Bay State Park and Madeline Island Museum as you discover Madeline Island—a family-friendly area also known for its island views.

See all hotels in Madeline Island

Top Madeline Island Hotel Reviews

Quality Inn Ashland - Lake Superior

10/10 Excellent

"The location and view of Lake Superior is amazing! The best part of the hotel is the view!"

The Washburn Inn - On the Lake

10/10 Excellent

"Enjoyed our stay! Staff was wonderful, room was clean, spacious shower with chair for accessibility. No complaints :)"

Hotel Chequamegon, BW Signature Collection

10/10 Excellent

"We thought that the food was really good, and the staff was very helpful! We had a long drive in, over six hours, and we were able to check in a little early, which was super helpful! The breakfast attendants were always doing a great job making sure there was fresh food and asking how things were. We had a couple questions that we asked the front desk, and they try to be as helpful as they could. The view was beautiful! We would definitely stay here again!"

Super 8 by Wyndham Ashland

10/10 Excellent

"It's an older Hotel, but it's still very nice for the price and the area. The room was quite, the beds are nice. Breakfast was very nice, There was a wide veriety to choose from."

Harbor's Edge Motel

8/10 Good

"Great location."

Cobblestone Inn & Suites - Ashland

10/10 Excellent

"Beautiful hotel and grounds"

Outbounder

10/10 Excellent

"Great place to stay. I was hoping for a view of the lake… maybe next time."

St. James Social

10/10 Excellent

"The check-in was odd. Thought there would be a desk. Also restaurant wasn’t open when we were there. Nice rooftop, lovely room. Very clean. They did provide beverages and occasional snacks. Not sure if this was supposed to be everyday. One day was lovely charcuterie and some breakfast things."

More cheap stays in Madeline Island

The Washburn Inn - On the Lake

123 Harbor View Drive Washburn WI

฿3,247

฿3,636 total

19 Oct - 20 Oct

includes taxes & fees

8.6/10 Excellent! (1,006 reviews)