Holiday rentals with a patio in Madeline Island

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.

Comfy Homebase for your Upper Peninsula Getaway

Centrally located 2 bed, 1.5 bath single family home all to yourself. Terrific floorplan with eat-in kitchen, large living + dining room with fireplace, 2 bedrooms and newly remodeled full bath. Powder Room on lower level. Just a few blocks to charming downtown Ironwood, Iron Belle Trail + close to Miners Park with trails for walking, mountain biking, snowshoeing, x-skiing. Quick access to all that’s amazing about the U.P.! If you love outdoor fun, this is the place to stay, relax + rejuvenate!

Park Place - Updated Home Close to Downtown

Enjoy our freshly renovated, boho themed home near the heart of downtown Ironwood, MI featuring 2 bedrooms (1 King, 2 Queen & 1 Twin bed) & 1 bath with a beautiful soaker tub. Great starting point for any local activity. Walking, biking, ATV & snowmobile trails only a few minutes away in any direction. Self check in, but always available for help. As loving pet owners, we do allow up to 2 well-behaved dogs. Group event? Book the house next door too (up to 13 guests): airbnb.com/h/greenhaveniwd

The Eclectic Apartment on Broad Street

Your jumping off point to all things Apostle Islands National Lakeshore. Rest and relax , one block from the public sauna and pool, where you will wake up to sunrises over Lake Superior and end your day on the deck with a glass of wine or a good book. The bedroom and living room have amazing natural lighting. Local coffee and a full kitchen, as well as laundry, free parking, Roku TV and a custom tile shower offer all of the comforts of home. The perfect romantic getaway, or a retreat for one!

Charming private cabin on Superior

Where to go for that peaceful retreat? Look no further than our humble gîte! Sip coffee on the porch, feel the breeze and hear the wind among the trees. Adventures by day: hike, fish or day trip to Grand Marais! The bike trail puts much in reach, jog to Gooseberry, bike to Split Rock, or stroll to Thompson Beach. In the evening the full kitchen is a dream for a foodie, or head fifteen minutes to a brewery. Before bed put up your feet, play a game, read a book, or doze by the fireplace’s heat.

The Acorn of Little Sand Bay Dog Friendly

Modern-rustic, Aframe on 10 wooded acres; beautiful, simple décor, fully equipped kitchen, glass stove top, air-fryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, with a heated tile floor, walk-in shower. Towels, shampoo/conditioner/bodywash are provided. King bed in loft and NEW king gel memory foam bed on main floor. Smart TV, wi-fi. Woodstove heats the cabin perfectly as the main heat source. All wood is provided for woodstove and firepit. There is a minisplit heat/ac unit.

Adorable Northwoods cabin

Come enjoy the North woods in our beautiful little cabin. This cabin is a located in a perfect spot only 2 miles outside of Iron River. Close to tourist areas such as Duluth, Bayfield, Ashland and more. This cabin is the perfect get away. The Brule river is only 8 miles away and can make for the perfect day trip in a kayak or canoe. This cabin comfortably fits 2-4 people! You can enjoy the outdoors at the fire pit or the 3 season porch that gives you the perfect indoor/outdoor feeling!

Haven House on Madeline Island

Come enjoy everything Madeline Island offers! Haven House is a well-maintained 2 bedroom, 2 bath cottage, less than 1 mile from the beach in either direction! Living room has an electric fireplace, TV with cable, and an upright piano. Kitchen is fully equipped! Things to do on the island: - Rent scooters and tour the island - Hike Big Bay State Park - Bike into town and visit local art galleries - Kayak the lagoon at Big Bay Town Park - Gift shops, restaurants, and ice cream shop!

South Shore A-Frame | Steps from Lake Superior

A peaceful, feel good place. Renovated rustic modern A-frame on 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.

Bright Updated Lakefront Home As Your Retreat

Welcoming all to this light-filled renovated cottage with three decks overlooking Superior to relax, sun, eat, play. On the side, a wetland with turtles, rabbits, birds, deer. Inside, an inviting open living room, big tv, nice full kitchen, new lux bathroom, two comfortable bedrooms, and cozy gas fireplace. We're the lucky new owners of this sweet cottage that is our part-time home and writing retreat, set up with all you need to come share in a bit of lake island life.

Moss Creek Cabin in the Woods on Madeline Island

Welcome to The Moss Creek Cabin! This chalet style home is a beautiful, sunny base for all of your island adventures and kicking back to relax in the woods. There is a large deck and a screen porch to lounge and hear all of the wildlife noises. You will be just 2 miles outside of town - far enough to be in nature - but also easy to get around, including walking and biking everywhere. The cabin is on 5 acres of private woods, so you will have plenty of space!

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!