Kid-friendly holiday rentals 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.

Kinney Valley Farm

This rustic, but modernized farmhouse is on 110 acres of woods and apple orchards. Snow is great now! Cross country ski trails are " skier-groomed" on our property. Multiple areas for groomed skiing are within 30-45 minute drives. Located just 3 miles from the south shore of Lake Superior, and 30 minutes from the Apostle Island Sea Caves, spectacular now with winter ice sculptures, Kinney Valley Farm is a cozy place to stay, while exploring the pastoral winter beauty of Northern Wisconsin.

Lakeview chalet by Gooseberry Falls with sauna

Spacious and family friendly chalet with sauna, game room, theater, kids room and more! Wake up to gorgeous views of Superior from your master bedroom, make breakfast in your fully equipped kitchen or drive two minutes to the Rustic Inn cafe, home to the best pie we've ever had (the North Shore mixed berry). After a busy day of exploring sites, from Gooseberry State Park to Split Rock Lighthouse, all within 10-15 minutes of your home base, you can unwind with beers at Castle Danger Brewery.

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

Hidden Vines - Walkable To Murals - Dog-Friendly

Renovated Old World Charm & a Tuscan/Vineyard vibe, this cozy 2 bedroom/2 bath is close to everything! Whether you are looking for relaxation or adventure, Hidden Vines is the perfect location-On a well-traveled road & only 4 blocks to downtown/main-street shops; 6 blocks to the Lake Superior/Bay & walking trail; and the lighted patio is the perfect spot for morning coffee/evening wine. We sleep 6 and are dog/kid friendly! Exterior GFCI and 3 off-street parking spaces for Trucks/Boats!

Come love the south shore of Lake Superior

The Cornucopia Sweet Retreat is a unique open concept living space above Corny Coffee in Cornucopia, Wisconsin. We are just steps from Lake Superior and the Cornucopia beach shops. Lost Creek Adventures is across the street and offers guided kayak tours to the sea caves, and Ehlers grocery store has wonderful deli sandwiches and salads. We are located 20 minutes from Bayfield, Wisconsin and the ferry to Madeline Island. The Cornucopia Sweet Retreat is a no smoking / no pet space.

Woodland Escape | Charming Cabin Steps to the Lake

Perfect for the whole family, including your canine companions! Woodland Escape combines the authentic Northwoods cabin vibe with modern comforts & a touch of whimsy (llama ottoman, anyone?). Located on a wooded 2.5 acre lot that is a short 5-minute walk to one of the area's loveliest beaches, this is a perfect place to relax, recharge, and reconnect with your loved ones. And it's in the perfect location on the South Shore with access to trails, towns, and the Big Lake!

The North Oak, a Modern Cabin

Make some memories at this unique and family-friendly home. Modern amenities with a modern cabin feel and small town charm. Brand-new, ranch style home with easy access. Big backyard with patio and fire pit. 3 blocks from Lake Superior and beaches. Walk/bike to downtown shops and restuarants. Great bike trails and kayaking, boating nearby. Close to ice fishing access, snowmobile trails and Mt. Ashwabay for winter fun!

7 Pines La Pointe on Madeline Island

NEED ISLAND SERENITY? Instant Book 7 Pines La Pointe on Madeline Island today! Come see how this 2 bedroom/2 bath cabin offers tranquility and peace in one of the more far away desired destinations in all of the country. Beautiful high peaked windows and glass doors, with a very large deck located in a forest of trees on the picturesque/historic Madeline Island, allow guests the feeling of going back in time.