Pet-friendly vacation rentals in Madeline Island

Cedar Ridge | Hand-Crafted Cabin with 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.

Outdoor spaces · Pets · Backyard

Walk to Shops & Lake/Hiking, EV Charger, Fire Pit!

Walk to downtown Bayfield, Lake Superior & top hiking trails from our stylish, pet-friendly home. Designed for families and groups, it features luxe beds, a fully stocked chef’s kitchen & cozy gathering spaces. Explore the Apostle Islands by day then unwind by the fireplace. ⭐ “We’ve stayed multiple times—it’s the perfect home-away-from-home in Bayfield!” 🌄 HIGHLIGHTS ✓ Walk to shops, restaurants & Lake Superior ✓ Fully stocked kitchen + EV charger ✓ Pet-friendly w/ fenced yard

Pets · Outdoor spaces · Access

Stunning Bark Point Home on Superior's South Shore

One of a kind, open/loft-concept (see pics: it really is open) artisan-crafted lake home on Superior's south shore: paddle in summer/ice hike in winter. Breathtaking sunsets. 300+ feet of private shoreline or short walk to public beach. Great kitchen. Up to 8 people and most dogs welcome - PET FEE: pets are an extra $25 (there is a place to leave this next to the house manual on the kitchen counter) Scenic huge patio with built-in fire pit (BYO firewood) We hope you love it as much as we do!

Walkability · Outdoor spaces · Checkout

Secluded Tiny Home w Nature Trail To Lake Superior

Enjoy a serene getaway in our private tiny home, nestled into the tree on the edge of town. This cozy 400 sq ft retreat features a fully equipped kitchen and a charming outdoor patio with a pergola. Clean lines plus an airy open floor plan make for a space that feels cozy and luxurious at the same time. Located just a 3-minute drive from Lake Superior, you can also take a short walk along the nature trail to reach the beach. Ideal for a peaceful and private escape. Reserve Little Blue today!

Pets · Outdoor spaces · Hospitality

Private lakefront retreat

Welcome yourself to the tastefully remodeled, Scandinavian-designed lake house with a sophisticated modern touch nestled on North Shore. Views of Lake Superior, Apostle Islands, and forested meadows seen from wrap-around, front porch & deck. Wood burning stove in open floor plan living & dining room perfect for family entertaining. Brand new appliances in updated kitchen connects to a large, screened-in porch. Enjoy the outdoors in large yard complete with fire pit & BBQ, or nearby hiking

Walkability · Outdoor spaces · Access

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.

Walkability · Outdoor spaces · Getting around

Sky Fire | Lake Superior Waterfront Retreat

Relax with expansive views of Lake Superior as you bask in the glow of the wood burning fireplace's radiance. Waves echoing off the brownstone cliff upon which this special home is perched, absorb the splendor of bald eagles soaring only feet away. Minutes from your nest is Meyer's Beach, the common entry point to begin your kayak or hiking excursion to the sea and ice caves of this, the greatest of all lakes. Bike, hiking, motorsports and XC ski trails abound. Rest or play. It's all here.

Outdoor spaces · Pets · Hiking

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!

Walkability · Outdoor spaces · Decor

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.

Outdoor spaces · Pets · Parks

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!

Outdoor spaces · Pets · Condition

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!

Pets · Outdoor spaces · Condition

Lake Superior Hillside Suite 1 • Walk Downtown

Relax in this peaceful hillside suite overlooking Lake Superior and Madeline Island. Wake to beautiful sunrise views and enjoy a short walk to downtown Bayfield’s restaurants, shops, marina, ferry, parks, and hiking trails. This cozy cottage-style apartment is the perfect home base for exploring the area while enjoying a quiet coastal retreat. 1 dog allowed (up to 60 lbs). Pets may not be left unattended in the suite. Please review house rules for details.

Walkability · Outdoor spaces · Indoor spaces