Holiday rentals with outdoor seating 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.

Cedar Ridge | Hand-Crafted Cabin with Lake Views

This newly built cabin will take your breath away. You’ll find the perfect blend of Northwoods rustic charm and creature comforts in this 3 bdrm cabin nestled in the woods overlooking Lake Superior’s Bark Bay. You’ll fall in love with all the care & attention its owners have put into every detail. From the stunning cedar beams that provide the backdrop to the incredible lake views to the hand-crafted interior woodwork and the beautiful kitchen, you will see how unique and special this cabin is.

Sky Fire | Lake Superior Waterfront Retreat

Relax with expansive views of Lake Superior as you bask in the glow of the wood burning fireplace's radiance. Waves echoing off the brownstone cliff upon which this special home is perched, absorb the splendor of bald and eagles soaring only feet away. Minutes from your nest is Meyer's Beach, the common entry point to begin your kayak or hiking excursion to the sea and ice caves of this, the greatest of all lakes. Bike, hiking, motorsports and XC ski trails abound. Rest or play. It's all here.

The Copper Squirrel of Little Sand Bay DogsWelcome

A mature forest and a beautiful pond are what you'll see when you arrive at this cozy, secluded, full log cabin. The cabin was recently completely renovated (Mar/April 2025)from log to log and is stocked with everything you'll need for your stay. It has all new appliances, furniture, fixtures, bathroom, cabinetry. 💚 It is the perfect homebase to relax after a long day of hiking Frog Bay, Houghton Falls, Lost Creek Falls, Meyers Beach, or shopping in nearby Bayfield, Washburn, or Cornucopia.

Superior Sanctuary: Refined Rustic in the Woods

Escape to the tranquil shores of Lake Superior in our charming retreat! Nestled within the serene Brickyard Creek Community, this modern haven offers a perfect blend of rustic elegance and contemporary comforts.  Immerse yourself in nature's beauty, unwind on the spacious screened porch, and cozy up by the fireplace. Your peaceful escape awaits. • Screened Porch with Swing Chairs • Access to Beach and Hiking Trails • Smart TV & Streaming • Modern Kitchen  • Boat Slip Rental Available

One Minute Walk to Lake Superior. Brookside #11

Amazing location! Updated Wifi in 2026. This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. AC, CableTV and fire pit wood provided. 1 minute walk to the marina. Bayfield is 2.3 mi from Brookside. Hike or bike the Brownstone trail along the lake. Take the ferry to Madeline, cruise the apostles, Sail, fish, kayak, golf, orchards, ski and more!! The pool and restraunt opens July 1st. 5 minutes from Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

Borealis Cottage by Siskiwit Bay

Borealis Cottage sits on a 2-acre, private, wooded lot in the sustainably designed Sawgrass Community of Cornucopia. Light-filled cottage with open floor plan includes a sleeping loft, screened porch, gas fireplace, and fully-equipped kitchen. A quick, quiet walk from the cottage takes you to a private wooded path with access to Cornucopia Beach on Siskiwit Bay. Explore the Apostle Islands National Lakeshore--our cottage is located 4 miles from Meyers Beach and 20 miles from Bayfield.

Hippophile Farm Get-a-way Garden Apartment

The space is a newly renovated apartment on the lower level of our home which is located at our private horse farm on Madeline Island. It is light, bright, with a modern and clean look. It has all the things you need to relax and rejuvenate after spending a day exploring Madeline Island. Enjoy the beautiful woods surrounding the apartment or take a walk to our beautiful stables on the property. Bring your horses if you wish, or just come to enjoy the scenery.

Lake Superior Getaway. Hillside Suites Unit #1.

Your inland coastal getaway in beautiful Bayfield, WI. Keep it simple at this peaceful and centrally-located place. Cottage apartment tucked into the hillside with wonderful views of Lake Superior and Madeline Island. Walking distance to restaurants, parks, hiking trails, ferry, and marina. We allow 1 dog up to 60 lbs. Dogs are not allowed to be left unattended in room (even if kenneled). Please read house rules section if bringing a pet for other guidelines.

The Red Onion House near Bayfield

Located 10 minutes s. of Bayfield, this is a casual, comfortable, and welcoming two-bedroom located across the highway from Lake Superior and the Apostle Islands and less than a mile from near the best beaches in the region. Named for the Onion River that flows nearby, this rental has a combo of pine floors & tile. Upstairs kitchen & dining area. Large lawn with easy, plentiful parking. Mt. Ashwabay, Big Top Chautauqua nearby. Outdoor patio + campfire area.

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.