Madeline Island places to stay

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Top-rated places to stay in Madeline Island

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Bayfield

4.97 out of 5 average rating, 109 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 favorite

Guest suite in Cornucopia

4.89 out of 5 average rating, 142 reviews

Apostle Islands Area Suite

Our lodging is located in Cornucopia, WI onsite to Lost Creek Adventures, a kayaking outfitter and only 4 miles from the Apostle Islands National Lakeshore. In the summer, we are a bustling outfitter - join us for a sea kayak tour or just relax at the beach. During the off-season (October through May) there are plenty of hiking, atv, and snowmobile trails in the area as well as local restaurants and beautiful sights. We are right across the street from Lake Superior and boast a beautiful sunset.

Guest favorite

Cottage in Two Harbors

4.93 out of 5 average rating, 110 reviews

Fox+FernCottage- Cozy family friendly downtown TH

Fox+Fern Cottage is your cozy home away from home. Our Cottage is walkable to nearly everything in Two Harbors. We are a mile walk to the lake and less than that to Castle Danger Brewery. Fantastic base to explore the North Shore (see reviews). Our yard is a quiet oasis with outdoor seating and swings galore. A/C units installed early JulyRarely will you needwith the cool lake breezes that flow through the shaded house. There's room to pitch a tent on the patio rubber mulch too . Permit #23-05

Guest favorite

Apartment in Two Harbors

4.94 out of 5 average rating, 162 reviews

Burlington View Stays License#1472

Relax in Northwoods themed lakeview apartment. One bedroom dog and kid friendly apartment with a lakeview from kitchen. Private entrance offers storage for outdoor gear and electric hookups for ebikes in the enclosed porch. There is off street parking for two vehicles or trailer. Centrally located on 7th avenue close to shops, restaurants, direct access to snowmobile trail routes and located near CC ski trails and hiking trails. Walking distance is less than three blocks to Burlington Beach.

Guest favorite

Treehouse in Iron River

4.92 out of 5 average rating, 61 reviews

Waterfront Tree House I Couples Retreat I Dogs OK

Fall graciously into autumn with your 5* stay at The Glass Tree House. Inclusive with all stays, an exclusive, luxury, wine and cheese cruise aboard the Lady Joanne. Take in the brilliant foliage and reflections on the sparkling waters of the Pike Lake Chain. The Glass Tree House truly is a special, private, couples retreat. Luxury amenities include plush robes/slippers and morning Caribou coffee in bed. Enjoy magnificent sunset views and the call of the loons at twilight on your private deck.

Guest favorite

Home in Bayfield

5 out of 5 average rating, 13 reviews

Serene Spot W/ Madeline Island/Lake Views & Sauna

-Modern, Spacious & Bright w/Great Vibes -Ideal Spot atop Bayfield on 1.56 Acres -Views of Madeline Island & Bayfield -Spacious lower level equally bright & airy -On a dead end street w/Ample parking -TV in each bedroom -Gateway to Apostle Islands -Near Downtown Bayfield & Marina - Wood-burning fireplace -Bonus lounge Room W/ a 65-inch TV, Bean Bags & board games - Fully equipped kitchen - Spacious Primary Bedroom W/ en-suite Bathroom & Deck Access **Special Pricing For Monthly/weekly stays

Superhost

Condo in Bayfield

4.81 out of 5 average rating, 277 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.

Superhost

Home in Two Harbors

4.85 out of 5 average rating, 330 reviews

Single or multiple nights-Winter discounts! #1419

* 25 min drive to Bentlyville * 5 blocks to EV charger * Off street trailer parking! * Blocks to Castle Danger Brewery * Fire pit w free firewood! Seasonal Grill Blocks to Lake Superior, Shops & Restaurants. We are nestled between Duluth & Gooseberry Falls A hammock available to use while hiking Work remotely in dedicated office space & fast WIFI..take your lunch break on the shores of the lake Huge yard to play games… grill, or just relax

Guest favorite

Cottage in Herbster

4.98 out of 5 average rating, 253 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.

Guest favorite

Farm stay in Maple

4.86 out of 5 average rating, 56 reviews

Wild Acres Lodge

Lots of room to roam with huge open spaces. Great fireplaces, charming rustic vibe, and total privacy. Unique floor plan! You must walk through bedrooms on upper floor to get to each bedroom. High quality everything! Lots of wildlife with great outdoor spaces too! Many snowmobile, ATV, and hiking trails right on the property! Great fishing, 4 miles from the historic Brule River! Home is approximately 30 minutes from Duluth. Check Out Our Video On YouTube! "Wild Acres Lodge Airbnb!!"

Superhost

Condo in Ashland

4.9 out of 5 average rating, 108 reviews

Main Street apt 2 blocks from Lake Superior!

STELLA South Shore Stay is a new, gorgeous, one bedroom apartment just two blocks from Lake Superior, located on Main Street in Ashland, WI. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, and much more. Walk to Lake Superior in minutes, get a coffee at the Black Cat or a pastry at the bakery, or enjoy the many restaurants and shops on Main Street. You can also enjoy the many local hikes or check out the Apostle Islands.

Guest favorite

Apartment in Two Harbors

4.96 out of 5 average rating, 207 reviews

Two Harbors Lodging Apt #5

Enjoy a get-away at this stylish apt located in the heart of downtown Two Harbors. Just a short walk from Agate Bay where you can watch ships come and go. Several eateries are within walking distance, as well as a local brewery. We are close to several state parks for the hiker, or the north shore explorer. Two Harbors also has an excellent golf course. Our Apt's offer you a cozy home-base to come back to after a fun day of exploring the north shore.