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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.

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Private Modern Home-Bear Paw Lodge

An outdoor enthusiasts get-a-way with step free entrance and accessible parking. A pet friendly place.This is a unique experience with great amenities and accommodations. 4 bathrooms for guest privacy Trails for ATVs Room for trailer parking Tucked up on the most northern point in Wisconsin. 2 miles away from a boat launch to the famous Apostle Islands, a beautiful beach, and park. There is something to do for any adventure. Just 12 miles away from Bayfield and Cornucopia there is easy access

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The Acorn of Little Sand Bay Dog Friendly

Welcome to my new modern-rustic, Aframe cabin in the woods... The Acorn. Beautiful, simple décor, fully equipped kitchen, new appliances, glass stove top, airfryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, heated tile floor, walk-in shower, shampoo/conditioner/bodywash provided. King-size bed in the loft area. Smart TV, wifi. Books, games, bluetooth speaker The woodstove heats the cabin perfectly in the colder months. All wood provided. There is also a minisplit heat/ac unit.

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Private 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

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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.

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Entire Home Near Lake Superior

Beautiful modern family home located in the quiet, little Town of Port Wing only 1.4 miles from the Lake Superior public beach and boat landing, and 2 blocks from National Scenic Byway Highway 13 (Lake Superior Circle Tour). Located centrally only 46 miles from Duluth and 35 miles from Bayfield. While staying here, you'll be able to enjoy the entire place to yourself, a specious backyard, large patio, off-street parking for 4 vehicles, outdoor dining, and a BBQ grille for your convenience.

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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!

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D’town Luxe | EV Charger, King Beds, Spa Bath

Welcome to your beautifully renovated historic home in the heart of Bayfield. This luxurious getaway offers king beds in spacious rooms, a gourmet kitchen and spa like bathrooms. You have central air and heat for guaranteed comfort. We offer one of Bayfield's only EV-chargers. Our home provides easy access to all Bayfield has to offer including beautiful Lake Superior, which is only a short walk away. 2 well behaved dogs allowed. $50/dog fee. Contact us for seasonal discounts!

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Boho Bunkhouse

Take it easy at this unique and tranquil getaway. Set in the north woods, 3 miles north of Iron River on the ATV/Snowmobile trails. *15 minutes from Lake Superior. *50 minutes from Bayfield *50 minutes from Duluth. Relax & read a book, hit the trails, or head to the lake. The South Shore area is filled with activities. Kayaking, fishing, hiking, swimming, waterfalls, ATV-UTV-Dirtbike riding and much more. Visit our local breweries, wineries, museums and nature center.

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SOUTH SHORE A-FRAME//Steps from Lake Superior

A peaceful, feel good place. Renovated rustic modern Aframe off 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.

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Seclusion in the Pines - A Hidden Gem in Bayfield

Rittenhouse Pines Cottage is a one-of-kind rental! It's a secluded getaway overlooking a ravine surrounded by towering pines. And it's close enough (seven blocks) to all downtown Bayfield has to offer! Since it's the guest cottage adjacent to our home (although it's about 1/2 block away), our three friendly dogs are used to having the run of the place. We'll keep them close to home during your stay but if you aren't a fan of dogs, this may not be the cottage for you.

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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!

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Sunny + Quaint Rental in the Heart of Bayfield

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Hobby Haven

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Walkable Bayfield 2bd / 1 bath w/ lake view + deck

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Easy access ground level condominium

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The Eclectic Apartment

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Luxury 2 bedroom lakeshore suite with roof deck

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Country in the City! Big Lake Views on 10 Acres

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Cozy Modern House Downtown Cable

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The Baron on 4th Street

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Best Lake Superior Views

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Lake Park House

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Adventure Homebase

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Hidden Vines - Walkable To Murals - Dog-Friendly

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Gichi Gami House Bayfield

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Hale House, Historic Gem

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