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.

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!

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.

Secluded Tiny Home w Nature Trail To Lake Superior

Enjoy a serene getaway in our private tiny home, nestled into the tree on the edge of town. This cozy 400 sq ft retreat features a fully equipped kitchen and a charming outdoor patio with a pergola. Clean lines plus an airy open floor plan make for a space that feels cozy and luxurious at the same time. Located just a 3-minute drive from Lake Superior, you can also take a short walk along the nature trail to reach the beach. Ideal for a peaceful and private escape. Reserve Little Blue today!

Bentleyville - 1 nite stays- 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.

The Acorn of Little Sand Bay Dog Friendly

Modern, rustic, Aframe cabin on 10 wooded acres; beautiful, simple décor, fully equipped kitchen, new 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-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.

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 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.

Bright Updated Lakefront Home As Your Retreat

Welcoming all to this light-filled renovated cottage with three decks overlooking Superior to relax, sun, eat, play. On the side, a wetland with turtles, rabbits, birds, deer. Inside, an inviting open living room, big tv, nice full kitchen, new lux bathroom, two comfortable bedrooms, and cozy gas fireplace. We're the lucky new owners of this sweet cottage that is our part-time home and writing retreat, set up with all you need to come share in a bit of lake island life.

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!

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 5 acres of woods, secluded from roads and neighbors. The cabin has an occupancy limit of 2 adults and one dog. There is a $40 pet fee.

Highland Hideaway

Quiet lake (canoe & kayak only). Fishing available. Close to numerous lakes with boat access. Adjacent to extensive ATV/snowmobile trail system. Restaurant/Bars nearby. If you enjoy shopping & sightseeing, Hayward is less than 30 min. away. 30 minutes or less drive to numerous golf courses. After your fun filled day, relax by the fire overlooking the lake.