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Greenwood in Union Pier, MI
Photograph: Courtesy Airbnb

16 lakefront Airbnbs to rent for a unique getaway from Chicago

Get out of the city with our pick of pretty lakeside retreats

Written by
Annalise Mantz
Emma Krupp
Georgia Evans
Lola Christina Alao

We all need a break from the hustle of bustle of city life once in a while. We might be hundreds of miles away from the nearest ocean, but that doesn't mean you can't book a relaxing vacation within just a few hours' drive from your home. For a weekend getaway near Chicago, consider these beautiful houses available for rental on Airbnb, which offer everything from stunning waterside vistas to private beaches. Whether you prefer quaint cottages atop the dunes near Lake Michigan, quiet farm stays or massive villas for entertaining a group, you're bound to find something you love among these fantastic lakeside properties. And there are tons to choose from, for your taste and needs. So don't wait, clear your calendar and start planning that much-deserved vacation.

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Lakefront Airbnbs near Chicago

With full views of the lavender, and the garden surroundings, this summer house will allows you to quickly wind down and unplug from the stressors of city life. A a unique, modern home that was constructed in 2013, it is fully furnished with Herman Miller and Knoll mid century furnishings. 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: a screened-in porch, queen-sized bed, kitchenette, and outdoor hot tub, all of which are sure to help you to unwind.


It's not a budget getaway— as the title clearly indicates —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.


Take advantage of the opportunity for relaxation with this lakeview home with full lake views from the dining table and deck. The beach boho vibes will make you feel like you're somewhere tropical. You really won't be stuck for stuff to do here either, from boating to river floating and hiking the 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. And another good thing about this property? It has 2.5 bedrooms, so no one will be fighting over who uses it first!


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. 


If you've never spent the night on a sailboat, this is your chance. You'll fall asleep to the sounds of the waves crashing and of seagulls. Enjoy some 'you' time, with the well thought out amenities at Reefpoint Marina including a hot tub to soak in. The 29-foot sailboat also boasts a microwave, fridge, and coffee maker aboard. The host might even throw in a free bottle of wine for you if you're lucky. 

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 boasts both a private beach and lap pool, so you have plenty of options for water activities. A group of friends could while away the hours 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 but 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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