Holiday rentals in Madeline Island

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Top-rated holiday rentals in Madeline Island

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Guest favourite
The living area features natural wood ceilings and large windows, allowing sunlight to fill the space. A comfortable gray sofa is positioned in front of a coffee table, and a small dining area includes a kitchenette with modern appliances and ample storage. Greenery is visible outside.
Cabin in La Pointe
4.95 out of 5 average rating, 37 reviews

Calm-365

This brand new Upper-Level Unit is located on the 7th Hole of Madeline Island Golf Course. Surrounded by old-growth white pines and green meadows, come and enjoy the natural scenic beauty from two spacious decks. Unit includes one full bedroom and bathroom (tub-shower ) with queen bed. Unit includes one queen pull out bed in living area. Full kitchen basic appliances. One K-cup style coffee maker, toaster, stove (with oven) ice maker in refridgerator. Gas fired grill with cooking utensils onsite

Guest favourite
A wooden pathway leads to the cottage, bordered by lush green grass and colorful flowers. The entrance is framed by wooden lattice, and a clear view of the lake can be seen through the trees in the background, highlighting the peaceful setting.
Cottage in La Pointe
4.95 out of 5 average rating, 55 reviews

Bright Updated Lakefront Home As Your Retreat

Welcoming all to this light-filled renovated cabin to relax, sun, eat, play. Outside, three decks and big yard overlook Superior right next to l ush wetland with turtles, rabbits, birds, deer. Inside, comfortable open living room and full kitchen, two cozy cool bedrooms, new lux bathroom. Big tv and gas fireplace, games and music, endless windows and views. We cherish this place and island as a part-time home and writing retreat and we love to have others come share in a bit of lake island life.

Guest favourite
A round table with a glass top is surrounded by four beige, woven chairs beneath a large umbrella. In the background, a vibrant garden features tall purple flowers and a green lawn, while a BBQ grill and fire pit are partially visible.
Camper van/Motorhome in La Pointe
4.85 out of 5 average rating, 226 reviews

Camp on Main Street

2017 28ft Jayco Camper. Located downtown La Pointe; walking distance to shops, cafes, restaurants, bars, ferry boat, museum, golf course, marina, boat rentals, swimming pool, playgrounds. 2 min walk to Joni's beach. Tucked in our beautiful back yard (private to renter, not used by owner) behind the house we live. So close to everything but yet in the quietest part of Main Street. Ideal for families or couples. Max occupancy 4-6. Every person above 4 (approved only by host) is $30.00 a night.

Top guest favourite
A spacious outdoor deck with a cozy lounge area featuring a modern propane fireplace surrounded by plush seating. The deck is lined with trees, providing a serene, private setting. String lights are seen above, adding ambiance to the inviting space for relaxation.
Cottage in Bayfield
4.99 out of 5 average rating, 120 reviews

Bayfield Fruit Loop Retreat - Main Cottage

Welcome to the Bayfield Fruitloop Retreat, featuring a beautiful "Main Cottage" nestled in 7 acres of woods in Bayfield, Wisconsin. The property allows you to savor a peaceful & quiet northwoods experience but still minutes from several attractions & historic downtown Bayfield. The property is conveniently located just 5 minutes' drive or 2.5 miles from the center of downtown Bayfield. Located right on country Hwy J, a starting point for a self-guided tour around the city of Bayfield where a

Top guest favourite
Cottage in Bayfield
4.87 out of 5 average rating, 194 reviews

Superior Sanctuary: Refined Rustic in the Woods

Escape to the tranquil shores of Lake Superior in our charming retreat! Nestled within the serene Brickyard Creek Community, this modern haven offers a perfect blend of rustic elegance and contemporary comforts.  Immerse yourself in nature's beauty, unwind on the spacious screened porch, and cozy up by the fireplace. Your peaceful escape awaits. • Screened Porch with Swing Chairs • Access to Beach and Hiking Trails • Smart TV & Streaming • Modern Kitchen  • Boat Slip Rental Available

Top guest favourite
The cabin's exterior displays a modern A-frame design, surrounded by a lush forest. The patio area features blue adirondack chairs and a small table, inviting relaxation amidst nature. A circular window enhances the aesthetic, creating a connection between indoor and outdoor spaces.
Cabin in Bayfield
4.99 out of 5 average rating, 221 reviews

The Acorn of Little Sand Bay Dog Friendly

Modern-rustic, Aframe on 10 wooded acres; beautiful, simple décor, fully equipped kitchen, glass stove top, air-fryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, with a heated tile floor, walk-in shower. Towels, shampoo/conditioner/bodywash are provided. King bed in loft and NEW king gel memory foam bed on main floor. Smart TV, wi-fi. Woodstove heats the cabin perfectly as the main heat source. All wood is provided for woodstove and firepit. There is a minisplit heat/ac unit.

Top guest favourite
A newly constructed cabin sits nestled among trees, featuring large picture windows and a screened porch. Nearby, a barrel sauna adds a rustic touch to the serene forest setting, with soft sunlight filtering through the treetops.
Cabin in Cornucopia
5 out of 5 average rating, 148 reviews

Romantic Forest Cabin, Sauna, Trail to Beach

Treat yourself to a deluxe stay in this quiet, newly constructed cabin with picture windows, screened porch and barrel sauna. Enjoy long days and sunsets at Corny Beach, a 10 min walk from the cabin along a nature trail. Visit Bayfield 20 min away or take in the quirky, small-town of Cornucopia and then come home and take a sauna in this peaceful forest! The cabin has an occupancy limit of 2 adults and one dog ($50 pet fee). A SUP board is stored near the beach for guests in summer.

Superhost
Cabin in La Pointe
5 out of 5 average rating, 3 reviews

North Channel Cabin on Madeline Island

Welcome to North Channel Cabin on Madeline Island, a small cabin with big views of Lake Superior and Apostle Islands National Lakeshore. Just a mile from Big Bay Beach, the cabin is thoughtfully finished to provide a comfortable place to relax while serving as the perfect basecamp for adventures in the area. Whether you’re exploring Madeline Island, visiting Bayfield, or discovering the Apostle Islands, North Channel Cabin is a welcoming spot to return to at the end of the day.

Guest favourite
A private outdoor patio is presented with a glass dining table surrounded by four chairs. Colorful flower pots with blooming plants add vibrancy to the space, complemented by natural stone and greenery. Steps lead up to the entrance of the home.
Farm stay in La Pointe
4.91 out of 5 average rating, 165 reviews

Hippophile Farm Get-a-way Garden Apartment

The space is a newly renovated apartment on the lower level of our home which is located at our private horse farm on Madeline Island. It is light, bright, with a modern and clean look. It has all the things you need to relax and rejuvenate after spending a day exploring Madeline Island. Enjoy the beautiful woods surrounding the apartment or take a walk to our beautiful stables on the property. Bring your horses if you wish, or just come to enjoy the scenery.

Top guest favourite
The spacious living area is illuminated by large windows allowing natural light to fill the room. A comfortable couch faces a wood stove, surrounded by greenery. A dining table is positioned nearby, enhancing the open layout with a cozy rug anchoring the space.
Cabin in La Pointe
4.97 out of 5 average rating, 32 reviews

Moss Creek Cabin in the Woods on Madeline Island

Welcome to The Moss Creek Cabin! This chalet style home is a beautiful, sunny base for all of your island adventures and kicking back to relax in the woods. There is a large deck and a screen porch to lounge and hear all of the wildlife noises. You will be just 2 miles outside of town - far enough to be in nature - but also easy to get around, including walking and biking everywhere. The cabin is on 5 acres of private woods, so you will have plenty of space!

Superhost
A spacious cabin nestled among trees showcases large peaked windows and a welcoming deck. Sunlight filters through the leaves, illuminating the cabin's wooden exterior and the surrounding forest foliage.
Cabin in La Pointe
4.84 out of 5 average rating, 261 reviews

7 Pines La Pointe on Madeline Island

NEED ISLAND SERENITY or SAND? Instant Book 7 Pines La Pointe on Madeline Island today and you can have both! Come see how this 2 bedroom/2 bath cabin offers tranquility and peace in one of the more far away desired destinations in all of the country. Beautiful high peaked windows and glass doors, with a very large deck located in a forest of trees on the picturesque/historic Madeline Island, which can give guests a feeling of going back in time.

Guest favourite
A rustic red yurt is surrounded by a forest of trees. A large wooden deck offers a welcoming entrance and is equipped with a sturdy railing. Natural ground covers and underbrush can be seen nearby, creating a serene and natural setting.
Yurt in Bayfield
4.95 out of 5 average rating, 396 reviews

Bayfield Rustic Yurt 2 (Terra Cotta)

Nestled in the middle of the Bayfield County Forest, this rustic, minimally maintained yurt has direct access to miles of non-motorized rec trails (mountain bike, cross-country ski and hiking). Enjoy panoramic views of Lake Superior including; Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton and Michigan) and the Upper Peninsula of Michigan. Come prepared to relax, unwind and explore the wonders of the north woods.

Popular amenities for Madeline Island holiday rentals

Frequently Asked Questions

  • Where is Madeline Island located?

    Madeline Island is part of the Apostle Islands in northern Wisconsin, sitting in Lake Superior. The island is known for its natural landscapes and local communities rooted in Indigenous and settler histories.

  • When is the best time to visit Madeline Island?

    Many visitors are drawn to Madeline Island in late spring through early fall, when temperatures tend to be milder, and outdoor activities are frequently suggested. Winter brings colder weather, favored by those interested in quiet landscapes and snow-based experiences.

  • What are some things to do near Madeline Island?

    You can explore historic sites, stroll along sandy beaches, or hike forested trails around Madeline Island. The area has opportunities for kayaking, biking, and visiting art galleries, along with experiencing local cultural traditions.

  • How is the weather near Madeline Island?

    Madeline Island has cold winters, with January temperatures often between 2–20°F (−16 to −7°C), and mild to warm summers, typically 56–78°F (14–25°C) in July. Visitors may want to prepare for changing weather and moderate precipitation throughout the year.