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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.

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!

Whispering Pines on Lake Siskiwit

Voted #1 as Northern Wisconsin's best airbnb vacation destination! Whispering Pines is located on the tranquil shores of Lake Siskiwit, just minutes from Cornucopia, Lake Superior, short drive to Bayfield, the gateway to the Apostle Islands, our road is part of the state off highway trail system. 1940's themed, 100 year old wood flooring throughout, modern furniture, new appliances, full-size bathroom, new stacked washer dryer, fast fiber optic internet, Roku TV. STRICT NO PET - ESA POLICY!

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!

Driftwood/Trails End Lodging/Entire Home

Set in the Northwoods small-town of Iron River. *15 mins to Lake Superior *50 mins to Bayfield *50 mins to Duluth Spend time hiking, boating, kayaking, fishing, canoeing, bicycling, swimming and more. Iron River/Bayfield county is famous for its ATV/UTV and Snowmobile trails. Located at the heart of the trail system, with easy access to the corridor, and a large parking area for trucks and trailers. Walking distance from most shops, restaurants and the local brewery and winery.

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.

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!

Beach Front Hideaway

Private beach with spectacular views. Kayaks available for a paddle out in the bay or enjoy a sunset from the deck. Also 2 bikes, fishingpoles, deck heaters, gas grills and a fire pit w/wood. Or Curl up with a good book in front of the indoor fireplace. 1 bed, 1 high end sofa sleeper. TV and Wifi, and a complimentary bottle of wine. A great retreat for 2 couples or a small group of friends. Only 8 minutes from downtown Ashland.

Romantic Vineyard Cabin, Sauna, Plunge Pool

Come and celebrate all that Bayfield has to offer at this quiet vineyard and forest getaway, just 2 miles from downtown. Located in Bayfield's charming Fruit Loop, you'll be surrounded by vines, forest, orchards, and berry farms. The Scandinavian cabin, forest facing sauna with plunge pool, and vineyard sit within acres of secluded woods. The cabin has an occupancy limit of 2 adults and one dog. There is a $40 pet fee.

Private, Modern Home w/Sauna | Lake & Island Views

🏡 Family-friendly vacation home ⭐ Sweeping views w/glowing reviews 🌲 1.56 acres privacy, Madeline Island view ☀️ Screened porch & large deck 🚗 Private dead-end street + ample parking 📺 TVs in all bedrooms 🔥 Wood-burning fireplace 🍳 Fully equipped kitchen 🛏 Primary suite w/bath + deck access 📍 Near downtown, marina & Apostle Islands 🎮 Bonus lounge: infrared sauna, 65” TV, bean bags & games 🍀 Nature all around