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Photograph: Courtesy Airbnb

18 lakefront Airbnbs to rent for a unique getaway from Chicago

Beat the heat at these stunning lakeside retreats.

Written by
Annalise Mantz
Emma Krupp
Georgia Evans
Lola Christina Alao

Sure, it's always nice to spend the day splashing around at your nearest Chicago beach—but when you're craving a little more in-depth relaxation along the water, a weekend getaway just might be in order. Fortunately, you'll find plenty of gorgeous lakefront Airbnbs within easy driving distance from Chicago that are perfect for skipping town for a couple days (or more). From tidy cottages with jet skis and private piers to palatial homes situated atop dunes overlooking Lake Michigan, there's truly a lake home for everyone's taste. Grab your swimsuit, bring your best beach read and prepare to unwind at these stunning lakefront Airbnbs near Chicago. 

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Lakefront Airbnbs near Chicago

With full views of the lavender and garden surroundings, this summer house will allows you to quickly wind down and unplug from the stressors of city life. Built in 2013, the home is decked out with Herman Miller and Knoll furniture for an artful midcentury touch. Wake up to the sunlight hitting your window and the lavender aromas in a cozy master suite with a dual walk-in shower. Hello relaxation!

Since it's not far from white-sand Oval Beach, the trail to Mount Baldhead and a plethora of local art galleries, this tiny house would be the perfect home base for a weekend of exploring all Saugatuck has to offer. The candy-apple red cottage might be small, but it has everything you need for a romantic getaway, including a screened-in porch, queen-sized bed, kitchenette and outdoor hot tub. 


Bring a whole crew of friends and family to hang out at this sprawling 5,000-square-foot lakehouse along the shores of Lake Shangrila in Bristol, Wisconsin. The property sits along more than 200 feet of shoreline complete with a small sandy beach area, plus a fire pit, grill and covered porch for enjoying sultry summer evenings. Inside, stretch out among seven bedrooms outfitted with a whopping total of five king beds and eight twin beds, plus a Peloton machine if you need to fit in a workout. 


It's not a budget getaway (as you'll note from the title) but this ultra-plush lakefront home offers cushy amenities and stunning views of the water nearly everywhere you look. Take in panoramic lakefront vistas from the living room's floor-to-ceiling windows or head outside and explore the surrounding nature areas; either way, you're in for a relaxing Lake Michigan getaway.

This cheery cottage sits atop a sandy bluff that offers pristine views of the Lake Michigan waters below. Start your morning taking in the lakeside vistas with coffee and breakfast on the back patio; from there, it's time to descend down a set of private stairs to enjoy a long day soaking up the sun at a 400-foot stretch of sandy beach. If you get bored (though we doubt you will), the nearby towns of South Haven and Saugatuck are full of cute shops and restaurants. 


Gaze across Channel Lake from this sweet two-bedroom home, which boasts massive windows for premium views of the water. You really won't be stuck for stuff to do here either, from boating to river floating and hiking the nearby nature preserves, plus much more. When you arrive, you'll be greeted by the master bedroom’s comfy king bed where you can sleep like a baby—though bedroom No. 2 also features a queen sized bed and two twin sized beds as well. 


Expand your sea glass collection at this Door County cottage, which features a leafy backyard overlooking the water and access to a secluded rock beach below. A fully-equipped kitchen invites cooking and baking, and while the tidy white-planked dining room is lovely, we recommend taking your breakfast at the outdoor table within eyeshot of the beach. 


Picture this: You spend Saturday morning at the farmer's market in nearby Holland, Michigan, picking up fresh bread, berries and veggies before returning to this little cottage on the lake. Then you head down the private beach below, weaving your way through grass-studded dunes, to have a picnic by the water. Such an idyllic lifestyle could be yours (for a few days, at least) when you stay at this charming rental.


This charming two-bedroom home features both a private beach and lap pool, so you have plenty of options for water activities. A group of friends could shoot the breeze while playing cards by the fireplace, whipping up meals in the open-concept kitchen and sipping drinks on the deck after a long day of fun happenings.


This cozy one-bedroom hideaway in Union Pier is just a short walk into town, where you’ll find small art galleries, cute cafes, local wineries and a well-loved public beach. After you return home for the evening, you can kick back on the screened-in porch, by an outdoor fire pit or beside the wood-burning fireplace.

Two blocks from both the Downer Avenue shopping district and Bradford Beach, this second-story residence has an eclectic vibe to match Milwaukee’s vibrant art scene. (Think palm print furniture, vintage wall art, a spiral staircase and a gorgeous maroon AGA range.) Four beds and a couch can comfortably sleep up to seven people, so you can round up the whole crew for a weekend getaway.


You want a motorboat with your Airbnb? You got a motorboat with your Airbnb. But to be fair, this glorious pad on Lake Como would be a draw even without the speeder. It’s at the end of a private road so you’ll get plenty of peace and quiet. If you want to venture out, there’s a great hiking trail on the Hermansen Conservatory just a few hundred yards from the house, plus downtown Lake Geneva is three miles away.

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