Family-friendly holiday rentals in Cook County

"Loftville": Sweet Lake Sup Loft near Grand Marais

Wonderful location for enjoying all that Grand Marais has to offer, while being slightly removed to enjoy the tranquil shoreline. Relax and listen to the waves crash from this newly buillt, charming, clean, and comfortable loft. Perched along the scenic lakeside, Croftville Road, you can enjoy the quiet Lake Superior life while being a short bike ride (use our bikes) to "the coolest small town in America", Grand Marais. Beautiful winter scenery at greatly discounted rates: check our calendar!

Storybook Northwoods Log Cabin on Lake Superior

Painted Rock sits perched on a quaint spit of ledge rock, halfway between Lutsen and Grand Marais, on the edge of Cascade State Park. This historic log cabin has been lovingly restored to retain all its original charm and history, while updated with all the luxury amenities. A large Main Room is home to a wood-burning fireplace, dining table, game table, and picture windows that bring the Big Lake indoors in all seasons. A bathroom with a deep soaker tub and heated floors adds spa-like comfort.

Cozy Timber Trails on Lake Superior

Our condo is the perfect hub for your next adventure! Spend the day taking advantage of the local activities/sights; or kickback, unwind, and enjoy the breathtaking views & cozy atmosphere of Chateau Leveaux. In addition to the pine walls & private fireplace that give you the feel of your very own north woods cabin, our unit also provides you with the comforts of home away from home. Hang out in the pool/hot tub/sauna/gameroom/lodge and enjoy the rooms walk out access to stunning Lake Superior!

Firefly (Private Rustic Log Cabin-View L Superior)

Firefly is a beautiful timber frame cabin on 2 acres of land w/ parking and a sauna! Surrounding windows offer views of pines & a small glimmer of Lake Superior. Perfect for solo adventures & couples willing to pack-in/pack-out. You are the CLEANER (you must vacuum, wipe, remove ALL food/garbage/rocks/crumbs and leave tidy!). It's fundamental to providing a healthy space for the next folks seeking a peaceful place to rest and rejuvenate. Near Superior Hiking Trail, Coho/Bluefin Bay, Lutsen

The Studio on Croftville Road

Come and enjoy what was originally built for an artist’s studio and converted to a pet-friendly cozy living space. The studio is a spacious 800-sq ft open-concept layout with charming skylights in the kitchen and bathroom, and windows to overlook Lake Superior. We’re located on Croftville Road, which locals call the "Walkers Road" - quiet to traffic and perfect for a casual stroll. Our delightful space comes with a balcony and deck access on the lake & the shore. BIPOC Welcome!

Mökki: Hovland Hut

This cozy cabin provides a perfect getaway and is a gem in all seasons, especially during the fall colors or a blowing winter storm. Timber frame cabin built on a hilltop, on 20 acres of old growth maples. Walls of glass, a screened in porch and a wrap around deck bring the outdoors inside. The ridge top location has spectacular views through the trees - with lake views after the leaves drop. The property also boasts a fantastic wood fired cedar sauna - perfect for rejuvenating.

Cozy Lake Superior cottage with a private beach!

A bright sunny cottage welcomes the whole family! Enjoy the power and beauty of Lake Superior from the deck or your beach. The cottage. built in 1935 by the Crofts, has been modernized and enlarged to be used all year around. Grand Marais is known as Artsy-it is reflected by the local art on the walls. Close to activities summer and winter you can choose to be busy or laid back and just enjoy the lake, the sun, the stars....and maybe a storm! Welcome to Shoreside!

Guesthouse at Hawkweed Farm

Looking for a comfortable basecamp from which to explore the North Shore? Our guest house offers spectacular views of Lake Superior, a queen size bed facing a wall of windows, a full kitchen & bath, and a relaxing living room. Look across the lake to the Apostle Islands or look across the universe at night! Hawkweed Farm sits on 30 bluff top acres 3 miles west of Grand Marais. Currently, it is home to llamas and chickens, and Oberhasli goats are coming soon.

Lake Superior A-Frame w/Sauna-Near GM+Dog Friendly

Float among the stars and aurora gaze in the hanging loft net. This idyllic woodland setting is home to fox, bear, deer, eagles, wolves, and even possibly a wandering moose. ⋇ Sauna ⋇ 1 min Walk to Lake Superior Beach ⋇ 9 miles from GM ⋇ Backyard Access to Superior Hiking Trail ⋇ Backs Superior National Forest ⋇ Seasonal Lake Superior Views ⋇ Built & operated by your local hosts. An ideal place for reconnecting with nature, a favorite person, and simple joys.