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

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.

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!

Beach Front Hideaway

Attention! G maps suggested route is incorrect. From Hwy 2 - left on 36th, right on Lake Park Rd. Private beach with spectacular views. Kayaks available for a paddle out in the bay or enjoy a sunset from the deck. Also deck heaters and gas grills and a fire pit w/wood. Or Curl up with a good book in front of the indoor fireplace. TV and Wifi too, and a complimentary bottle of wine. A great retreat for 2 couples or a small group of friends. Only 8 minutes from downtown Ashland.

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!

A Cozy Getaway in Ashland

Welcome to your perfect getaway! This cozy 2-bedroom, 1-bath home is centrally located just a short walk from downtown, a bakery, brewery, and two blocks from Lake Superior. Enjoy direct ATV/snowmobile trail access, relax on the deck, or gather around the firepit. Take a walk or bike ride along the scenic lake trail or explore nearby shops. Only 30 minutes from Bayfield and 90 from Duluth-perfect for day trips or a relaxing retreat.

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

Private, Modern Home w/Sauna | Lake & Island Views

🏡 Family-friendly vacation home ⭐ Sweeping views w/glowing reviews 🌲 1.56 acres privacy, Madeline Island view ☀️ Screened porch & large deck 🚗 Private dead-end street + ample parking 📺 TVs in all bedrooms 🔥 Wood-burning fireplace 🍳 Fully equipped kitchen 🛏 Primary suite w/bath + deck access 📍 Near downtown, marina & Apostle Islands 🎮 Bonus lounge: infrared sauna, 65” TV, bean bags & games 🍀 Nature all around