Vacation rentals in Madeline Island

4.93 out of 5 average rating, 257 reviews

A rustic A-frame cabin is set amidst tall trees, featuring a stone pathway leading to a fire pit with stacked logs. Outdoor seating is visible, and a patio umbrella provides shade, enhancing the inviting outdoor space.

Cabin in Herbster

South Shore A-Frame | Steps from Lake Superior

A peaceful, feel good place. Renovated rustic modern A-frame on Lake Superior's scenic south shore. Surrounded by evergreen and birch trees in an idyllic woodland setting. Enjoy walks to the beach (1/4th mile down road), breathtaking sunsets and beach bonfires, kayaking the famous seacaves, biking, hiking to waterfalls, shopping for vintage treasures or just relaxing/stargazing in the beautiful private backyard. A perfect home base for exploring the Apostle islands, Bayfield and Madeline Island.

4.95 out of 5 average rating, 56 reviews

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

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.

4.85 out of 5 average rating, 228 reviews

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/RV in La Pointe

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.

4.99 out of 5 average rating, 120 reviews

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

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

4.87 out of 5 average rating, 194 reviews

Cottage in Bayfield

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

4.99 out of 5 average rating, 221 reviews

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

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.

4.99 out of 5 average rating, 409 reviews

A charming red cottage is nestled among tall trees, showcasing a welcoming front with two white Adirondack chairs placed on a natural surface. Decorative flower arrangements hang near the entrance, surrounded by lush greenery and plants.

Guesthouse in Ashland

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

5 out of 5 average rating, 148 reviews

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

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.

4.75 out of 5 average rating, 4 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.

4.99 out of 5 average rating, 159 reviews

The modern home is surrounded by lush greenery, with large windows reflecting the evening light. A staircase with railings leads to the entrance, enhancing accessibility. A circular window adds a unique architectural feature, while soft lights illuminate the exterior, creating a serene nighttime ambiance.

Cabin in Herbster

Superior Sunsets @ The West Slope (Steam Shower)

Our 3 bedroom, 2 bath home is located 1 mile out of Cornucopia and 20 miles from Bayfield. Nestled in a lush forest on a sandstone cliff overlooking Lake Superior, this home is a new build featuring a STEAM SHOWER , a fully equipped kitchen and cozy gas fireplace . Deck with grill and stunning sunset views. Large entertainment room w/ 65" Smart T.V. , POOL TABLE & DART BOARD. Outdoor firepit and picnic table. WE PRACTICE ENHANCED SANITIZING MEASURES WITH EVERY TURNOVER.

4.91 out of 5 average rating, 165 reviews

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

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.

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.

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.

Popular amenities for Madeline Island vacation rentals

Free parking on premises

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Madeline Island house rentals

4.9 out of 5 average rating, 81 reviews

An aerial view captures the lake house and boathouse nestled among trees along a sandy shoreline. The gentle waves lap against the beach, framed by lush green foliage and rocky outcrops. The tranquil setting offers a serene escape beside the waters of Lake Superior.

Home in Herbster

Private Beach Haven with All of the Comforts

4.8 out of 5 average rating, 20 reviews

A serene lakeside view captures the sun setting over calm waters. Two rustic chairs are positioned on the shore, framed by trees. The horizon glows with warm colors, reflecting off the lake's surface, while surrounding foliage adds to the tranquil atmosphere.

Home in La Pointe

Private lakefront retreat

4.91 out of 5 average rating, 23 reviews

Home in La Pointe

Unique Custom Built Home on Madeline Isalnd

4.87 out of 5 average rating, 185 reviews

A small wooden dining table is positioned against the wall, accompanied by two white, spindle-back chairs. A light plaid table runner is placed across the table. Natural light filters in through a nearby window, creating a warm and welcoming dining space.

Home in Ashland

Bungalow (House) on Chequamegon Bay.

4.97 out of 5 average rating, 426 reviews

The exterior of an artisan-crafted lake home is shown at twilight, featuring large windows that reflect the soft evening light. Surrounded by greenery and wildflowers, a stone pathway leads to the entrance, enhancing the natural setting.

Home in Herbster

Stunning Bark Point Home on Superior's South Shore

4.91 out of 5 average rating, 47 reviews

A view of Lake Superior is captured from a spacious deck, showcasing snow-covered ground and a table at the center. Pine trees are present in the foreground, framing the tranquil water and a pastel sky at dusk. The setting offers a peaceful ambiance.

Home in Ashland

Water Street Retreat by The Lake

4.75 out of 5 average rating, 394 reviews

A red two-story house with a green metal roof is set within a natural landscape. A gravel driveway leads up to the home, which features several windows and a large yard. A parked blue car is positioned near the entrance.

Home in Washburn

The Red Onion House near Bayfield

4.94 out of 5 average rating, 67 reviews

A spacious living area is complemented by green walls and large windows that provide natural light. A comfortable sectional sofa is arranged around a circular coffee table. A bookshelf filled with books adds character, while decorative plants bring an element of nature indoors.

Home in Ashland

Adventure Homebase

Other great vacation rentals in Madeline Island

4.91 out of 5 average rating, 229 reviews

The interior features warm wooden walls and a cozy seating area with a leather couch and colorful cushions. A small dining table with iron chairs sits nearby, complemented by large windows allowing natural light. Stairs lead to a loft area, enhancing the space's openness.

Treehouse in Bayfield

Boulderridge Treehouse

4.89 out of 5 average rating, 19 reviews

A modern tiny house features large glass windows framed with wooden slats, allowing natural light to fill the interior. It is surrounded by a lush green landscape, with wildflowers visible in the foreground, adding to the serene setting.

Cabin in Bayfield

Modern Tiny House w/Lake Superior View

Home in La Pointe

5 out of 5 average rating, 4 reviews

The Haven on Madeline island by Wilder Co

4.99 out of 5 average rating, 78 reviews

A tranquil campfire area is set near Lake Superior, featuring a fire pit surrounded by wooden benches and chairs. The scene is framed by trees, with the lake and a sunset in the background, creating a serene outdoor gathering space.

Cabin in Ironwood

!!Private Beach Access!! ~Cozy Lake Superior Cabin

4.88 out of 5 average rating, 16 reviews

A vibrant sunset casts warm hues across the sky over the water. People walk along a pathway bordered by a white railing, while a boat moves gently across the water, contributing to the tranquil atmosphere. The shoreline includes rocks and trees, adding natural elements to the scene.

Apartment in Bayfield

Madeline Island Lakeview Condo

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.

4.97 out of 5 average rating, 33 reviews

Moss Creek Cabin in the Woods on Madeline Island

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.

4.95 out of 5 average rating, 37 reviews

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