Holiday rentals with a patio in Bayfield County

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.

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

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.

Willow North Cottage in Iron River, Wisconsin

Enjoy this newly renovated, cozy, two-bedroom cottage all on a no public access lake in the Northwoods! Sip on your morning coffee among the tall pines, or watch the sunset on the back deck overlooking the lake. The cottage feels very remote being on this private lake, but not far from many premier attractions. We are located just 5 minutes from the town of Iron River, in Bayfield County. Features a private keypad entry, queen-sized bed, bunk beds, kitchen, private deck with stairs & more!

Blueberry Cottage - Singing Sands on Lake Superior

Take it easy at this unique & tranquil getaway. Located in Siskiwit Bay right on this very sandy beach of Lake Superior. A private path from the cabin will lead to a pristine walk out shallow beach. See Romans Point, Siskiwit Bay Marina and Eagle Island from the very front of this floor to ceiling view! This 500 square foot cabin is neat and compact & newly remodeled. This is one of the best stretches of beaches the area has to offer. Over 200 feet of owned shoreline for you to enjoy.

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.

The Acorn of Little Sand Bay Dog Friendly

Modern, rustic, Aframe cabin on 10 wooded acres; beautiful, simple décor, fully equipped kitchen, all appliances, glass stove top, airfryer 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 bed on main floor. Smart TV, wifi. Books, games The Woodstove heats the cabin perfectly in the colder months. All wood provided. There is also a minisplit heat/ac unit.

Bayfield on the Lake - Waterfront Condo (#303)

Unit #303 at Bayfield on the Lake is the premier place to stay in Bayfield while exploring the town, Madeline Island, and the Apostle Islands. Located directly on the harbor, there is no better view in town. Walking distance to everything including shops, the Madeline Island Ferry Line, beaches, playgrounds, dining, and more. With 4 bedrooms, a game room that includes a foosball table, a kitchen with brand new appliances, this condo is perfect for large groups looking to get away.

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.