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 balcony with wicker furniture, a small table, and a view of a marina with boats and cars.

A covered outdoor area with a wooden deck, potted plants, and a brick wall.

A compact kitchen with a sink, microwave, and coffee maker. There is a wooden chair and a small table.

A bathroom with a white door, a sink with a mirror, and a framed picture on the wall.

1. Harbor's Edge Motel

Bayfield

Grace

Rp2.154.805

Rp2.456.471 total

includes taxes & fees

5 Oct - 6 Oct

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

A compact kitchenette with a coffee maker, microwave, and a small refrigerator.

2. Lakeside Motel

Ashland

Patti

Rp1.342.725

Rp1.504.031 total

includes taxes & fees

12 Oct - 13 Oct

A marina filled with various boats at sunset.

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

An aerial view of a marina with boats docked, a parking lot, and buildings with a large parking area.

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

3. The Washburn Inn - On the Lake

Washburn

Michael

Rp1.463.570

Rp1.639.199 total

includes taxes & fees

19 Oct - 20 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.

4. Hotel Chequamegon, BW Signature Collection

Ashland

DOROTHY

Rp3.204.816

Rp3.589.395 total

includes taxes & fees

18 Oct - 19 Oct

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

A bar area with a wooden counter, bar stools, a television, and a sign indicating breakfast is available for 40.

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

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

5. Cobblestone Inn & Suites - Ashland

Ashland

jolene

Rp2.561.919

Rp2.869.349 total

includes taxes & fees

20 Oct - 21 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 modern kitchen with dark wood cabinets, a large stove, and a microwave.

A two-story log cabin with a stone foundation, a green roof, and a balcony overlooking a lake.

6. Quality Inn Ashland - Lake Superior

Ashland

Tammy

Rp3.028.292

Rp3.391.687 total

includes taxes & fees

27 Oct - 28 Oct

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

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

A hotel room with a large bed, a chair, a lamp, and a view of the water through the windows.

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

7. Blue Wave Inn

Ashland

Dawn

Rp2.400.792

Rp2.688.886 total

includes taxes & fees

22 Oct - 23 Oct

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

A hotel room with two beds, a TV, a desk, and a chair.

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

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

8. AmericInn by Wyndham Ashland

Ashland

Jonathan

Rp2.846.577

Rp3.188.345 total

includes taxes & fees

27 Oct - 28 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 pool area with wooden walls, a pool, and several chairs.

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

9. Super 8 by Wyndham Ashland

Ashland

Ann

Rp2.345.293

Rp2.626.728 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

A large, two-story house with a steeply pitched roof, stone foundation, and a prominent front porch.

10. Pinehurst Inn - Luxury Bayfield Hotel

Bayfield

Carrie

Rp3.532.799

Rp3.956.735 total

includes taxes & fees

26 Oct - 27 Oct

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

A wooden staircase with white railings leading to a lofted area. A bench with cushions is placed against the wall below the staircase.

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

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

11. Seagull Bay Motel

Bayfield

Melissa

Rp2.658.596

Rp3.030.799 total

includes taxes & fees

29 Sept - 30 Sept

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

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

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

A modern kitchen with white cabinetry, stainless steel appliances, and a patterned rug.

12. Mission Springs Resort

Ashland

Brian r

Rp2.646.833

Rp2.792.408 total

includes taxes & fees

27 Oct - 28 Oct

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

A modern bedroom with a large bed, a wooden chair, a small table, and a hanging light fixture.

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

A sauna room with wooden benches and a large window.

13. St. James Social

Bayfield

Rp6.345.503

Rp7.233.875 total

includes taxes & fees

21 Oct - 22 Oct

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

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

A view from a room with a door leading to a deck overlooking a body of water and a forested area.

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

14. Legendary Waters Resort & Casino

Bayfield

Michael

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

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

A cozy room with wicker furniture, a small table with a lamp, and a view through large windows.

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

15. Outbounder

Bayfield

Helen

Rp2.953.995

Rp3.367.733 total

includes taxes & fees

29 Sept - 30 Sept

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

A bedroom with a bed, a nightstand, a wooden ceiling, a kitchenette, and a window with curtains.

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

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

16. The Mill House

Bayfield

Christopher

Rp4.363.856

Rp4.974.886 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

A rocky shoreline with clear water and lush greenery.

Top Madeline Island Hotel Reviews

Lakeside Motel

10/10 Excellent

"Perfect place. Very clean. Matter of fact...Spotless. Quiet,great location. Wonderful view of lake. Fridge, microwave, Kerrigan style coffee maker with several flavor pods. They are pet friendly (dog). As you know places that welcome pets are not easy to find. Be responsible and walk your pet and clean up after it. The price is perfect. I got 1 night stay, 2 people. None of the 2 night high price stuff. I'd only add 1 thing. For those of us with back surgeries, bad joints, getting older, a handicap bar by toilet would be great. Has big screen tv. For us the stay was PERFECT!"

The Washburn Inn - On the Lake

8/10 Good

"Nice room and clean. Staff is nice. We love that it’s close to Bayfield."

Harbor's Edge Motel

10/10 Excellent

"Clean room and peaceful area. Also within walking distance to many businesses and the marina. Highly recommend for a stay in Bayfield."

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."

Outbounder

10/10 Excellent

"Room was clean, nice and quiet, within walking distance to nearby amenities"

Seagull Bay Motel

10/10 Excellent

"The room was just about perfect for what we were looking for. Nice kitchenette, bed was comfortable, air conditioning worked well and this was a very nice location for the walk on the path into town. Only 10 minutes and we were in the midst of the restaurants and also the boat tour and ferry to Madeline Island."