Holiday rentals with outdoor seating in Madeline Island

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Top-rated rentals with outdoor seating in Madeline Island

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Bayfield

4.97 out of 5 average rating, 101 reviews

Captain's Cabin

Centrally located in the heart of downtown Bayfield--this charming, ground-level condo is just steps away from restaurants, coffee shops, and a block from City Dock and the Lake. The 830 sq.ft condo sleeps 4. A spacious bedroom holds a king bed while the living room has queen sleeper sofa. Located in the historic George Crawford House on one of Bayfield's classic brick lined streets, private parking is provided at the rear of the building with a short walk to the best of everything in Bayfield.

Guest favourite

Cottage in Herbster

4.92 out of 5 average rating, 315 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

Cabin in Herbster

4.97 out of 5 average rating, 101 reviews

Cedar Ridge | Hand-Crafted Cabin w/Lake Views

This newly built cabin will take your breath away. You’ll find the perfect blend of Northwoods rustic charm and creature comforts in this 3 bdrm cabin nestled in the woods overlooking Lake Superior’s Bark Bay. You’ll fall in love with all the care & attention its owners have put into every detail. From the stunning cedar beams that provide the backdrop to the incredible lake views to the hand-crafted interior woodwork and the beautiful kitchen, you will see how unique and special this cabin is.

Guest favourite

Chalet in Bayfield

4.98 out of 5 average rating, 129 reviews

The Acorn of Little Sand Bay Dog Friendly

Welcome to my new modern-rustic, Aframe cabin in the woods... The Acorn. Beautiful, simple décor, fully equipped kitchen, new appliances, glass stove top, airfryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, heated tile floor, walk-in shower, shampoo/conditioner/bodywash provided. King-size bed in the loft area. Smart TV, wifi. Books, games, bluetooth speaker The woodstove heats the cabin perfectly in the colder months. All wood provided. There is also a minisplit heat/ac unit.

Guest favourite

Cottage in Bayfield

4.86 out of 5 average rating, 132 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

Guest favourite

Cabin in Ironwood

4.95 out of 5 average rating, 471 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, 347 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

Cabin in Herbster

4.93 out of 5 average rating, 164 reviews

SOUTH SHORE A-FRAME//Steps from Lake Superior

A peaceful, feel good place. Renovated rustic modern Aframe off Lake Superior's scenic south shore. Surrounded by evergreen and birch trees in an idyllic woodland setting. Enjoy walks to the beach, 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.

Guest favourite

Yurt in Bayfield

4.94 out of 5 average rating, 428 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

Home in Ironwood

4.99 out of 5 average rating, 209 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!

Guest favourite

Cottage in Herbster

4.99 out of 5 average rating, 172 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

Home in La Pointe

4.95 out of 5 average rating, 119 reviews

Henny Penny-Quiet and Close to Town

This home is located on beautiful Madeline Island! It is less than a mile from the ferry dock and all that the town of La Pointe has to offer including beaches, shops, restaurants/ bars, galleries, kayak rental, the marina, the golf course and more! You can easily bike or walk to town. A nice and quiet location for low key evenings on the deck. The home is not visible from the road adding extra privacy.