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.

Cozy Trailside Nordic Forest Cottage

Welcome to the Trailside Gökotta Forest Cottage: a modern, minimalist and serene nature cabin on the Birkie Trail system. Gökotta means 'to get up early to listen to sounds of birds and the forest'. Located right on Birkie Ridge Trailhead with close access to vast CAMBA trails, this is a nature escape for outdoor enthusiasts who love to bike, ski, hike, and bird watch. Enjoy ski-in ski-out to groomed trails, bike-in bike-out right onto trails, then cozy up by the woodstove or fire-pit at night.

Comfy Homebase for your Upper Peninsula Getaway

Centrally located 2 bed, 1.5 bath single family home all to yourself. Terrific floorplan with eat-in kitchen, large living + dining room with fireplace, 2 bedrooms and newly remodeled full bath. Powder Room on lower level. Just a few blocks to charming downtown Ironwood, Iron Belle Trail + close to Miners Park with trails for walking, mountain biking, snowshoeing, x-skiing. Quick access to all that’s amazing about the U.P.! If you love outdoor fun, this is the place to stay, relax + rejuvenate!

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!

Architect-designed, net zero home w/ stunning view

Great for a couple's getaway or family excursion, perfectly located on the North Shore with a spectacular view of Lake Superior. Features stunning timber frame modern design, luxurious master bed and bath, spacious deck, and porch with fireplace. There's nothing else like it on the North Shore. It is perfectly located 20 minutes from Duluth and 5 minutes from Two Harbors, 5 from a boat launch. Our cabin is certified as Net Zero Ready through the DOE and was designed and built by Timberlyne.

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.

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.

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!

Studio A of The Studios @ 123

Convenient location in downtown Two Harbors one block from the shores of Lake Superior where you can take a short walk to view the majestic ore boats load and unload or hike the trails along the lakeshore. Afterwards you can enjoy a cold brew at the famous Castle Danger Brewery or a delicious homemade meal from Louise's Place. All within 1 block of the apartment. Two Harbors is the gateway to the North Shore of Lake Superior where your adventure begins.