
Holiday houses in Madeline Island
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Top-rated holiday rentals in Madeline Island
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Other great holiday rentals in Madeline Island

Treehouse in Bayfield
4.93 out of 5 average rating, 199 reviewsBoulderridge Treehouse
CalebRating, 5 stars8 months ago
The treehouse was fantastic. We were looking to see some fall colors and get away to a quiet place for some recharging rest. We got just that, with Bayfield right down the street and orchards galore. Beautiful space!

Home in La Pointe
4.73 out of 5 average rating, 11 reviewsPrivate lakefront retreat
MarkRating, 5 stars9 months ago
If we head back to Madeline Island, this is the place to stay. Great views & the cabin offers a variety of living spaces. Beds were comfortable. The screened porch is spacious & the main house offers a large great room with several seating areas. Interior was nicely appointed. Sharp drop-off to the water, so really no access from the cabin. There's a nice beach a couple miles away. Running trash / recycling over to the Island's landfill takes about an hour total, but not too much of a hassle. We really had a nice visit.

Boat in Bayfield
4.53 out of 5 average rating, 170 reviewsDowntown Irish Sailboat
KimberlyRating, 5 stars8 months ago
Tyler let us know everything we needed to find the marina, boat and how to get in. It was just like the listing. It was a very interesting experience!
Guest favourite

Private room in La Pointe
4.88 out of 5 average rating, 25 reviewsSiren’s Landing - Funky Island Cabin in the Woods
HannaRating, 5 stars3 days ago
Staying at Kelsey’s place was an absolute dream! From the moment I arrived, I felt welcomed and completely at home. The space was spotless, beautifully decorated, and full of thoughtful touches that showed how much care Kelsey puts into hosting. Communication was easy and kind—she was always quick to respond and so helpful with anything I needed. One of the unexpected highlights of my stay was getting to meet her sweet dog and her brother’s dog—they were both so well-behaved, friendly, and just adorable! It made the stay feel even warmer and more special. The neighborhood was peaceful and convenient, and I slept better than I have in weeks. Thank you, Kelsey, for such a cozy, relaxing, and memorable getaway. I’d 100% stay here again and recommend it to anyone looking for a truly welcoming place to stay. 💛

Cabin in La Pointe
4.61 out of 5 average rating, 85 reviewsMagical Handcrafted Cabinilicious in Magazines
JessicaRating, 5 stars8 months ago
Beautiful place and location. We loved the cabin’s kitschy personality. Yes the stairs are steep but we were anticipating that based on other reviews. It worked out fine for us. We had small dogs with us that were carried up and down the stairs when went to bed in the evening. Couple small things would have made the stay a little more comfortable. A few board games for rainy days. A couple basic cooking items like oil, sugar and garlic powder. The pillows are pretty beat up and could use replacing. All of these things are pretty easily overlooked though for the location alone. Woodsy and magical and so close to Big Bay Town Park. We thoroughly enjoyed our long weekend in this beautifully crafted cabin.

Home in Herbster
5 out of 5 average rating, 3 reviewsTimber & Tide Retreat
KristyRating, 5 stars2 weeks ago
Our stay at Timber & Tide was wonderful! The view of Lake Superior was spectacular! The outdoor space was perfect with a firepit, wood, chairs, hammocks and grill. The inside had a stocked kitchen and very nice decor. It was a very peaceful stay and we were appreciative that we could bring our dog.
Top Guest favourite

Cabin in Ashland
5 out of 5 average rating, 6 reviews"Our Cabin" on Lake Superior
MichelleRating, 5 stars1 week ago
We absolutely loved the cabin, and were just feet off of Lake Superior and the view was spectacular. We enjoyed spending time by the campfire and watching the boats in the bay and wildlife. The cabin was spotless and Nancy went above and beyond with the special extra amenities she provided. She also made homemade cookies and delicious crackers. We couldn’t have asked for a better host or place to stay!
Guest favourite

Apartment in Bayfield
4.9 out of 5 average rating, 52 reviewsWonderstate Bayfield Sunny 2-bedroom Apartment
CarolineRating, 5 stars3 weeks ago
We had a perfectly lovely stay here. Walking distance to all the shops/restaurants, and real close to where you can catch the ferry to Madeline Island. Loved that it was above Wonderstate Coffee, we made sure to go there each day we were there! Would totally stay again!
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