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Madeline Island vacation rentals

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Top-rated vacation rentals in Madeline Island

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Yurt in Bayfield

4.86 out of 5 average rating, 443 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.

Aug 20 – 27

G$16,030 GYD per night

Camper/RV in La Pointe

4.83 out of 5 average rating, 167 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.

Sep 17 – 24

G$29,494 GYD per night

Condo in Bayfield

4.8 out of 5 average rating, 258 reviews

One Minute Walk to Lake Superior. Brookside #3

Amazing location! No cleaning fee! This Condo sleeps 4, King bed & Queen sofa sleeper. Full kitchen, balcony, AC, CableTV, WiFi, BBQ, fire pit, and bikes. Restaurant, bar and pool in July-Sept.Bayfield is a 2.3 mile hike or bike on the Brownstone Trail. Brookside is 5 minutes from Mt Ashwabay, Big Top, Bayview beach and multiple hiking trails. Ride a ferry ride to Madeline or cruise the Apostles. Sail, fish, kayak, golf, ski. Pool opens in July. $40 pet fee per stay. 🙂 No smoking allowed.

Dec 13 – 20

G$26,266 GYD per night

Cottage in Herbster

4.98 out of 5 average rating, 211 reviews

Lake Superior's Cranberry River Cottage- The Raven

Enjoy beautiful Lake Superior in the 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 Nat'l Forest or venture to Bayfield, home of the Apple Fest, or visit the Apostle Islands Nat'l Lakeshore to see the sea/ice caves.

Jan 27 – Feb 3

G$25,272 GYD per night

Guesthouse 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.

Dec 15 – 22

G$40,310 GYD per night

Tiny home in Saxon

5.0 out of 5 average rating, 132 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.

Jan 12 – 19

G$24,876 GYD per night

Yurt in Bayfield

4.9 out of 5 average rating, 140 reviews

Turtle Yurts - Yurt 2

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.

May 11 – 18

G$24,612 GYD per night

Yurt in Bayfield

4.94 out of 5 average rating, 401 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!

Feb 13 – 20

G$24,261 GYD per night

Home in Ironwood

4.99 out of 5 average rating, 186 reviews

"Bakery Bungalow" -Sweet Accommodations & Nature !

Completely remodeled from head to toe! Located within half mile of trail system, 2 miles from historic downtown shops, on the outskirt of town (Ironwood Township=great drinking water) minutes from Big Powderhorn Mountain & Copper Peak, walking distance to Gogebic College & Mount Zion, 17 miles from Lake Superior, large private wooded yard with fire pit in summer, private parking, 1 stall garage if needed in winter. A light Bakery breakfast included with your stay!

Jan 16 – 23

G$27,441 GYD per night

Cottage in Herbster

4.99 out of 5 average rating, 138 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!

Oct 29 – Nov 5

G$30,792 GYD per night

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.

May 6 – 13

G$46,690 GYD per night

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.

Nov 5 – 12

G$42,667 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Madeline Island vacation rentals

Laptop-friendly workspace

Air conditioning

Other great vacation rentals in Madeline Island

Home in Bayfield

4.97 out of 5 average rating, 187 reviews

Star View House

Sep 20 – 27

G$59,863 GYD per night

Home in Ashland

4.88 out of 5 average rating, 121 reviews

Bungalow (House) on Chequamegon Bay.

May 14 – 21

G$29,942 GYD per night

Home in Ironwood

4.99 out of 5 average rating, 145 reviews

On the Trail-Cedar Sauna & Close to Ski & Trails

Aug 7 – 14

G$34,604 GYD per night

Home in Port Wing

4.9 out of 5 average rating, 177 reviews

Kinney Valley Farm

May 2 – 9

G$23,785 GYD per night

Home in Ironwood

4.98 out of 5 average rating, 216 reviews

The House Next Door, In-Town Two Story House

Jul 31 – Aug 7

G$26,065 GYD per night

Home in Mason

4.94 out of 5 average rating, 237 reviews

Marengo River Cabin

Dec 17 – 24

G$37,867 GYD per night

Home in Washburn

4.93 out of 5 average rating, 125 reviews

Up North Oasis | Groups & Dogs in Bayfield Area

Nov 12 – 19

G$39,889 GYD per night

Home in Ironwood

4.97 out of 5 average rating, 103 reviews

Park Place - Updated Home Close to Downtown

Oct 12 – 19

G$32,061 GYD per night

Madeline Island cottage rentals

Cottage in Bayfield

4.83 out of 5 average rating, 108 reviews

Superior Sanctuary: Refined Rustic in the Woods

Feb 13 – 20

G$75,238 GYD per night

Cottage in Cornucopia

4.98 out of 5 average rating, 108 reviews

Escape to the Lake at Corny Cottage

Feb 14 – 21

G$50,778 GYD per night

Cottage in Washburn

4.97 out of 5 average rating, 101 reviews

Lake Superior Cottage

Sep 11 – 18

G$55,222 GYD per night

Cottage in La Pointe

4.96 out of 5 average rating, 26 reviews

Bright Updated Lakefront Home As Your Retreat

Sep 12 – 19

G$49,182 GYD per night

Cottage in La Pointe

5.0 out of 5 average rating, 27 reviews

Haven House on Madeline Island

Jan 8 – 15

G$61,204 GYD per night

Cottage in Bayfield

4.98 out of 5 average rating, 52 reviews

Bayfield Fruit Loop Retreat - Main Cottage

Jan 21 – 28

G$39,866 GYD per night

Cottage in Cornucopia

4.98 out of 5 average rating, 96 reviews

Borealis Cottage by Siskiwit Bay

Sep 27 – Oct 4

G$38,437 GYD per night

Cottage in Iron River

4.86 out of 5 average rating, 35 reviews

Willow North Cottage in Iron River, Wisconsin

Jan 1 – 8

G$35,749 GYD per night

Other great vacation rentals in Madeline Island

Cabin in Bayfield

4.98 out of 5 average rating, 273 reviews

The Copper Squirrel of Little Sand Bay Dogs OK

Feb 22 – Mar 1

G$48,554 GYD per night

Chalet in Bayfield

4.98 out of 5 average rating, 101 reviews

Northwoods Chalet @ Brickyard Creek

Sep 23 – 30

G$53,394 GYD per night

Cabin in Herbster

4.94 out of 5 average rating, 140 reviews

SOUTH SHORE A-FRAME//Steps from Lake Superior

G$34,628 GYD per night

Guest suite in Cornucopia

4.93 out of 5 average rating, 117 reviews

Apostle Islands Suite

May 30 – Jun 6

G$29,858 GYD per night

Cabin in Herbster

5.0 out of 5 average rating, 104 reviews

Superior Sunsets @ The West Slope (Steam Shower)

May 6 – 13

G$74,658 GYD per night

Guesthouse in Two Harbors

4.97 out of 5 average rating, 117 reviews

Swan Forest Loft - trees are your neighbors

Aug 11 – 18

G$31,036 GYD per night

Cabin in Solon Springs

4.97 out of 5 average rating, 152 reviews

Valley Red Cabin

Mar 21 – 28

G$27,176 GYD per night

Guest suite in Cornucopia

4.98 out of 5 average rating, 129 reviews

Come love the south shore of Lake Superior

Oct 10 – 17

G$32,820 GYD per night

Destinations to explore