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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Our top choices for Madeline Island hotels

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

1. Seagull Bay Motel

Bayfield

Dave

4.406.743 ₫

5.023.687 ₫ total

includes taxes & fees

24 Oct - 25 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.

2. St. James Social

Bayfield

Michelle

7.867.040 ₫

8.968.425 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

3. Hotel Chequamegon, BW Signature Collection

Ashland

Brian

3.305.186 ₫

3.701.809 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A marina filled with various boats at sunset.

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

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

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

4. The Washburn Inn - On the Lake

Washburn

Amy

3.592.594 ₫

4.023.964 ₫ total

includes taxes & fees

25 Oct - 26 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 modern restaurant with a bar area, seating, and a large window offering a view of the street.

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

5. Cobblestone Inn & Suites - Ashland

Ashland

Caleb

4.163.791 ₫

4.663.653 ₫ total

includes taxes & fees

31 Oct - 1 Nov

A hotel room with a large bed, a chair, a wooden floor, a radiator, a window with curtains, a lamp, a painting, and a robe hanging on the door.

A wooden staircase leading to a loft area with a view of the outdoors.

A cozy living room with a fireplace, leather sofas, and a table with a glass of wine and a fruit platter.

A two-story house with a prominent gabled roof, a front porch, and a well-lit entrance.

6. Pinehurst Inn - Luxury Bayfield Hotel

Bayfield

3.972.349 ₫

4.449.030 ₫ total

includes taxes & fees

6 Nov - 7 Nov

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

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

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

Lexi

3.576.569 ₫

4.005.757 ₫ total

includes taxes & fees

22 Nov - 23 Nov

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

A beach with turquoise chairs and a pile of logs.

A hotel room with a large window, a sofa, a desk with a computer, a television, and a bathroom with a mirror and sink.

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

8. AmericInn by Wyndham Ashland

Ashland

Jonathan

3.233.335 ₫

3.621.542 ₫ total

includes taxes & fees

22 Nov - 23 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 coffee maker, microwave, and a small refrigerator.

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

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

9. Lakeside Motel

Ashland

Cheryl

1.938.450 ₫

2.171.322 ₫ 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 sandy beach with kayaks and fishing rods.

A balcony with a view of a calm body of water, a metal railing, and two chairs.

10. Blue Wave Inn

Ashland

Jonah

2.302.879 ₫

2.579.431 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

11. Outbounder

Bayfield

Helen

5.039.970 ₫

5.745.824 ₫ 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 pool area with wooden walls, a pool, and several chairs.

A hotel room with a leather sofa, a small cabinet with a television, and a patterned floor.

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

12. Super 8 by Wyndham Ashland

Ashland

John

3.349.642 ₫

3.751.547 ₫ 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 beach with a sandy shore, trees, and a body of water.

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

13. Mission Springs Resort

Ashland

Brian r

5.275.686 ₫

5.565.848 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

14. Legendary Waters Resort & Casino

Bayfield

Michael

A modern living room with a brown leather sofa, a round coffee table, and two armchairs.

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

A house with a wooden deck, a garage, and a garden area.

A two-story house with a balcony, surrounded by a garden with various plants and flowers.

15. The Mill House

Bayfield

Christopher

6.623.038 ₫

7.550.134 ₫ total

includes taxes & fees

26 Oct - 27 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.

See properties

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

The Washburn Inn - On the Lake

8/10 Good

"For the price, disappointed there isn't some kind of breakfast. There is just a few rooms with a lake view. Our view was the parking lot. They did give out a voucher for a free app with entree purchase at the restaurant next door. The staff is very friendly."

Cobblestone Inn & Suites - Ashland

8/10 Good

"Great location, parking can be a bit tight, very clean facilities, check in staff did not let us know what amenities were available and forgot to mention the included breakfast available on the first floor. They did provide us with complementary toothpaste when we forgot ours which was very helpful. Overall we enjoyed our stay and loved the Ashland area."

Quality Inn Ashland - Lake Superior

8/10 Good

"Food was good, location good, pool and hot tube clean. Our fridge smelt like rotten food, but other than looking rustic...so not always a bad thing...it was comfy and quiet...not run down."

Hotel Chequamegon, BW Signature Collection

10/10 Excellent

"Classic feel. Huge rooms. Nice bar."

Lakeside Motel

10/10 Excellent

"Cost was great value for accommodations! Loud next to highway during the day but was quiet at night. Bed was very firm, but I slept good."

The Mill House

8/10 Good

"We rented the place for a girls weekend and the location was absolutely perfect. Beautiful view of the lake and within walking distance of all the shops and restaurants. The only downside was the awkward seating with uncomfortable furniture in the living area and a lack of amenities in the kitchenette. There were no coffee cups and a wine fridge rather than a small fridge/freezer meant we had no ice. All in all a lovely stay and would be even better with a few changes!"

Outbounder

10/10 Excellent

"I had a good experience with the staff and appreciated the Bun̈ coffee machine. The room was warm and clean."

More cheap stays in Madeline Island

Super 8 by Wyndham Ashland

1610 Lake Shore Dr W Ashland WI

3.349.642 ₫

3.751.547 ₫ total

31 Oct - 1 Nov

includes taxes & fees

Quality Inn Ashland - Lake Superior

30600 Us Highway 2 Ashland WI

3.576.569 ₫

4.005.757 ₫ total

22 Nov - 23 Nov

includes taxes & fees

8.8/10 Excellent! (1,003 reviews)

The Washburn Inn - On the Lake

123 Harbor View Drive Washburn WI

3.592.594 ₫

4.023.964 ₫ total

25 Oct - 26 Oct

includes taxes & fees

8.6/10 Excellent! (1,001 reviews)

Cobblestone Inn & Suites - Ashland

818 Main Street W. Ashland WI

4.163.791 ₫

4.663.653 ₫ total

31 Oct - 1 Nov

includes taxes & fees

9.4/10 Exceptional! (862 reviews)

Seagull Bay Motel

325 South 7th Street Bayfield WI

4.406.743 ₫

5.023.687 ₫ total

24 Oct - 25 Oct

includes taxes & fees

Harbor's Edge Motel

33 North Front Street Bayfield WI

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Book Hotels in Madeline Island on Expedia.com

Find hotels in Madeline Island, WI from 2.171.322 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Madeline Island

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Madeline Island hotels

1. Seagull Bay Motel

2. St. James Social

3. Hotel Chequamegon, BW Signature Collection

4. The Washburn Inn - On the Lake

5. Cobblestone Inn & Suites - Ashland

6. Pinehurst Inn - Luxury Bayfield Hotel

7. Quality Inn Ashland - Lake Superior

8. AmericInn by Wyndham Ashland

9. Lakeside Motel

10. Blue Wave Inn

11. Outbounder

12. Super 8 by Wyndham Ashland

13. Mission Springs Resort

14. Legendary Waters Resort & Casino

15. The Mill House

Stay near popular Madeline Island attractions

Big Bay State Park

Madeline Island Museum

Learn more about Madeline Island

Top Madeline Island Hotel Reviews

The Washburn Inn - On the Lake

Cobblestone Inn & Suites - Ashland

Quality Inn Ashland - Lake Superior

Hotel Chequamegon, BW Signature Collection

Lakeside Motel

The Mill House

Outbounder

More cheap stays in Madeline Island

Super 8 by Wyndham Ashland

Quality Inn Ashland - Lake Superior

The Washburn Inn - On the Lake

Cobblestone Inn & Suites - Ashland

Seagull Bay Motel

Harbor's Edge Motel

Explore a world of travel with Expedia

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