Holiday houses in Red Cliff

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

Bayfield Fruit Loop Retreat - Main Cottage

Welcome to the Bayfield Fruitloop Retreat, featuring a beautiful "Main Cottage" nestled in 7 acres of woods in Bayfield, Wisconsin. The property allows you to savor a peaceful & quiet northwoods experience but still minutes from several attractions & historic downtown Bayfield. The property is conveniently located just 5 minutes' drive or 2.5 miles from the center of downtown Bayfield. Located right on country Hwy J, a starting point for a self-guided tour around the city of Bayfield where a

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

Bayfield on the Lake - Waterfront Condo (#303)

Unit #303 at Bayfield on the Lake is the premier place to stay in Bayfield while exploring the town, Madeline Island, and the Apostle Islands. Located directly on the harbor, there is no better view in town. Walking distance to everything including shops, the Madeline Island Ferry Line, beaches, playgrounds, dining, and more. With 4 bedrooms, a game room that includes a foosball table, a kitchen with brand new appliances, this condo is perfect for large groups looking to get away.

Grandma’s Country Cottage/Sleeps 8/Dog-Friendly

Comfortable, Quiet Grandma's Country Cottage has a Vintage Vibe & has been in the Family Since the 80's. The owner's grandparents built the home, it's a very special place for Her. 4brms/1.5baths - Space for everyone to spread-out. Huge eat-in kitchen & dining space. Large living room with enough couches for everyone to relax. Old school linoleum floors & ridiculous shag carpet. Not much has been changed at all! (The building at the foot of the drive is not part of the Airbnb.)

North Channel Cabin on Madeline Island

Welcome to North Channel Cabin on Madeline Island, a small cabin with big views of Lake Superior and Apostle Islands National Lakeshore. Just a mile from Big Bay Beach, the cabin is thoughtfully finished to provide a comfortable place to relax while serving as the perfect basecamp for adventures in the area. Whether you’re exploring Madeline Island, visiting Bayfield, or discovering the Apostle Islands, North Channel Cabin is a welcoming spot to return to at the end of the day.

Henny Penny-Quiet and Close to Town

This home is located on beautiful Madeline Island, less than a mile from the ferry dock and all La Pointe has to offer—beaches, shops, restaurants/bars, galleries, kayak rentals, marina, golf course and more! Easily bike or walk to town. Enjoy quiet evenings on the deck and added privacy, as the home is not visible from the road. Less than 1 mile from the Madeline Island Marathon start line and the Fourth of July parade and fireworks! 🎆

Fox Hollow Hideaway Just minutes from the beach

Cozy North Shore Cabin – Bayfield, WI Escape to this charming two-bedroom, 2 Full bathroom cabin on Lake Superior’s north shore in Bayfield, WI. Surrounded by towering pines, this cozy retreat offers a warm living space, a fully equipped kitchen, and a peaceful deck. Just minutes from town, hiking trails, and the Lake Superior, it's the perfect spot for relaxation or adventure. Book your stay and experience the beauty of Bayfield!

Island View Retreat

Enjoy a cozy retreat to Bayfield, Wisconsin & the Apostle Islands! Island View Retreat is a cozy apartment overlooking Madeline Island and Long Island. The apartment has a private entrance for guests, 2 bedrooms, full kitchen, full bathroom & comfortable living room area. Island View Retreat is conveniently located 0.5 Miles from the heart of downtown Bayfield. A 10 minute walk to coffee shops, restaurants, city dock and more!

Madeleine Lane Cottage

Cozy 1 bedroom cottage with a gas fireplace in the living room and electric fireplace in the bedroom. You will love the fully equipped kitchen, bathroom, large screened in porch with dining table for lounging, eating or playing games. Enjoy the sweet sounds of Brickyard Creek waters nearby. There is a pull out couch in the living room for more sleeping options. All nestled in a boreal forest on the shores of Lake Superior.

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.