Vacation 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.

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!

Twist & Shout

No matter what your age you will never forget the experience of staying at the North Shores only RETRO Vacation Rental! Vinyl records, retro popcorn machine, 3 large screen TV's, electric fireplace, unique decor, makes this truly a special retreat. This special getaway will not disappoint. Walking distance to several restaurants,gift shops and of course ice cream. Six blocks from Minnesota famous Castle Danger Brewery, 1000ft ore boats,or take a walk on the unforgettable breakwall and breathe!

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.

Lake/Dine/Drink - Sleeps 8/Dog-Friendly

Hip Nautic is the perfect combination of boho meets mid-century modern. Kid & dog friendly. Whimsical decisions can be made from the moment you arrive. In the mood to chill? Refreshing coffee/tea bar & front porch will hit the spot! Backyard firepit, & dog runner cable. Attn: Outdoor enthusiasts-walking distance to Lake Superior. Short distance to Ski/snowboard/snowmobile trails, golf, Superior Hiking Trail, State Parks w/waterfalls, mountain biking, rock climbing. Walk to shop/dine/drink.

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!

Off grid glamping at a Rockhound Hideaway

A perfect glamping retreat awaits you at Rockhound Hideaway's Agate Grove Bell Tent. Situated on a private two acre lot with two other rentals and my private residence in the Ottawa National Forest, steps from the Black River, North Country Trail and a one mile walk to the Lake Superior Shore, this is an ideal getaway for those seeking the adventure of camping with the comforts of home. Fall asleep to the sound nature and wake up to deer passing by as you enjoy your morning coffee.

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.

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!