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Holiday rentals in Madeline Island

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Top-rated holiday rentals in Madeline Island

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Yurt in Bayfield

4.87 out of 5 average rating, 446 reviews

Bayfield Rustic Yurt 1 (Evergreen)

Explore thousands of acres of the Bayfield County Forest and enjoy endless miles of exceptionally maintained non-motorized recreational trails. The yurt has direct access to CAMBA mountain bike trails and Mt. Ashwabay ski trails. The landscape is also spectacular. Take in the panoramic views of Lake Superior and the Onion River valley. This is a rustic, minimally maintained yurt set in the middle of the county forest, so come prepared to relax, unwind and explore the wonders of the north woods.

Guest favourite

Cottage in Herbster

4.91 out of 5 average rating, 279 reviews

Lake Superior's Cranberry River Cottage- The Wren

Enjoy beautiful Lake Superior in this clean cozy modern cottage located in the quaint little town of Herbster where the Cranberry River enters. It's just a short couple blocks to the beach and playground. Enjoy the beautiful sunsets, swimming, boating, kayaking, biking, fishing, hunting, and skiing with ATV and snowmobile trails nearby. Explore the Chequamegon National Forest or venture to Bayfield, home of the Apple Fest, or visit Apostle Islands National Lakeshore to see the ice/sea caves.

Guest favourite

Campervan/Motorhome in La Pointe

4.83 out of 5 average rating, 168 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.

Guest favourite

Cabin in Ironwood

4.95 out of 5 average rating, 420 reviews

The Shell Cabin at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Shell Cabin, with opportunities for hiking, biking, fishing, boating and everything in between. Take in the views from your back deck, relax around the bonfire, enjoy walk to Lake Superior, hike or snowshoes the North Country Trail to waterfalls or take a day trip to the Porkies. Don't forget to visit Downtown Ironwood and experience its charm for yourself. Amazing star gazing and Northern Lights potential! 420 Friendly for 21&up.

Guest favourite

Guest house in Ashland

4.99 out of 5 average rating, 310 reviews

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.

Guest favourite

Tiny home in Saxon

5.0 out of 5 average rating, 136 reviews

Parker Creek Tiny House

Come stay on our hobby farm with us! We are in a great central location to multiple hiking trails and gorgeous falls. We have had many guests visit the sea caves in Cornucopia, spend the day in Bayfield, or hike the Porcupine Mountains. We also are only a few miles from the ATV trails if you would rather spend the day riding the trails. We have multiple places to mountain bike or kayak. We have more things to do listed in our details section! Feel free to message me with questions.

Guest favourite

Yurt in Bayfield

4.92 out of 5 average rating, 146 reviews

Turtle Yurts - Yurt 1

1 Bedroom, 1 Bath, Sleeps 2 Nestled among the north woods, this yurt has everything you need for a comfortable and unique getaway. The design is a contemporary twist on the traditional yurt, featuring classic yurt elements such as lattice walls and radial rafters, along with modern amenities. The yurt sleeps up to two guests with a queen-size bed sitting under a clear dome to watch the sky above. There is a sitting area, as well as a bathroom, complete with shower and flush toilet.

Guest favourite

Yurt in Bayfield

4.94 out of 5 average rating, 402 reviews

Twisting Twig Gardens and Orchard Rustic Yurt

Our yurt offers a sweet retreat in the woods about 10 miles outside of Bayfield. We are located on a small working organic farm with vegetable gardens, apple trees, and rustic accommodations. We are close to great outdoor recreation near Lake Superior and are about 6 miles from Meyers Beach in the Apostle Islands National Lakeshore. Our property is located on 40 acres and is very remote. We are on the edge of thousands of acres of county land. The perfect escape!

Guest favourite

Cottage in Herbster

4.99 out of 5 average rating, 140 reviews

Applegate Cottage - South Shore of Lake Superior

Applegate cottage is an adorable cottage located just a short walk from the beautiful beach in Herbster, Wisconsin on the Lake Superior Scenic Byway. Whether you like hiking, biking, kayaking, skiing or just relaxing, there’s something nearby for everyone. Bayfield County has orchards, wineries, the Apostle Islands, sea caves, boutique shopping, waterfalls, great restaurants and so much more! Best of all…the sunsets! And, every season brings it’s own beauty!

Guest favourite

Cabin in La Pointe

4.85 out of 5 average rating, 197 reviews

7 Pines La Pointe on Madeline Island

NEED ISLAND SERENITY? Instant Book 7 Pines La Pointe on Madeline Island today! 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, allow guests the feeling of going back in time.

Guest favourite

Cabin in Bayfield

4.98 out of 5 average rating, 275 reviews

The Copper Squirrel of Little Sand Bay Dogs OK

A mature forest and a beautiful pond are what you'll see when you arrive at this cozy, secluded, full log cabin. The cabin is completely stocked with everything you'll need for your stay; from utensils and spices to toiletries and towels. It is the perfect homebase to relax after a long day of hiking Houghton Falls, Lost Creek Falls, Meyers Beach, or shopping in nearby Bayfield, Washburn, or Cornucopia.

Guest favourite

Farm stay in La Pointe

4.94 out of 5 average rating, 125 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 our beautiful stables on the property. Bring your horses if you wish, or just come to enjoy the scenery.

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Other great holiday rentals in Madeline Island

Guest favourite

Apartment in Bayfield

4.83 out of 5 average rating, 120 reviews

One Minute Walk to Lake Superior. Brookside #10

Guest favourite

Apartment in La Pointe

4.99 out of 5 average rating, 91 reviews

#1 Lakeside

Guest favourite

Flat in La Pointe

4.93 out of 5 average rating, 90 reviews

Treehouse 2 on Madeline Island

Guest favourite

Cottage in La Pointe

4.96 out of 5 average rating, 26 reviews

Bright Updated Lakefront Home As Your Retreat

Guest favourite

Cottage in La Pointe

5.0 out of 5 average rating, 27 reviews

Haven House on Madeline Island

Guest favourite

Flat in Bayfield

4.94 out of 5 average rating, 50 reviews

Country in the City! Big Lake Views on 10 Acres

Guest favourite

Flat in La Pointe

4.8 out of 5 average rating, 30 reviews

Suite One at La Pointe Lodging

Guest favourite

Cabin in Bayfield

4.98 out of 5 average rating, 55 reviews

Romantic Vineyard Cabin, Sauna, Plunge Pool

Destinations to explore