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17 lakefront Airbnbs to rent for a unique getaway from Chicago

Beat the heat at these stunning lakefront Airbnb retreats.


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 of 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

The tiny oriole in Saugatuck
Photograph: Courtesy Airbnb

1. The tiny oriole in Saugatuck

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. 

The Lake Michigan chalet in Stevensville
Courtesy: Airbnb

2. The Lake Michigan chalet in Stevensville

Watch gorgeous sunsets from this lakefront Airbnb near Chicago in Stevensville, Michigan. Offering direct beach access from the front door, this is a water lover's dream Airbnb. Sleeping up to six guests in two bedrooms, the space is ideal for families who love to explore the outdoors, and the communal pools and playgrounds offer even more fun ways to spend your trip. The rustic and charming decor gives a cozy vibe, and the fully-equipped kitchen provides the option of cooking home-cooked meals before taking them out on the decking and watching the world go by. 

The cozy retreat in Belding
Courtesy: Airbnb

3. The cozy retreat in Belding

Perfect for a winter getaway, this lakefront Airbnb near Chicago is located on Big Pine Island Lake in Belding. Catering for up to ten guests, the Airbnb has a rustic and characterful feel, but with modern touches to ensure a comfortable stay. Make use of the private hot tub and games room, before chilling by the outdoor fire pit, watching the sunset across the lake. Immaculate vibes.  

The luxury lake house on Wonder Lake
Courtesy: Airbnb

4. The luxury lake house on Wonder Lake

Looking to stay right on Lake Como? Well, this is the lakefront Airbnb for you. Just under 90 minutes drive from Chicago, this luxury lakehouse has so much to offer. From cozy fireplaces and homey extras to wraparound decking and lakefront access, this place is ideal for a family trip away from the city. The house sleeps 12 guests across four bedrooms and has four bathrooms to match. And if you're keen on water sports, you can hire jet skis, kayaks, canoes, or even a pontoon – with the choice of captain or not! 

The shorefront chalet in Sturgeon Bay
Photograph: Courtesy Airbnb

5. The shorefront chalet in Sturgeon Bay

This Door County home has a vintage nautical vibe, thanks to views of Sturgeon Bay, lake-themed decor and a shape that mimics the hull of a ship. Make good use of the rowboat, kayaks and fishing gear at the backyard pier, then bust out the board games after night falls. Feeling romantic? Hunker down outside to watch the sunset over the water.

The grand lodge on Lake Shangrila in Bristol
Photograph: Courtesy Airbnb

6. The grand lodge on Lake Shangrila in Bristol

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. 

The Lake Michigan cottage in South Haven
Photograph: Courtesy Airbnb

7. The Lake Michigan cottage in South Haven

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. 

The writer’s cabin in Kenosha
Photograph: Courtesy Airbnb

8. The writer’s cabin in Kenosha

Whether you plan to work on your novel or prefer to spend your days boating around Lake Michigan, this peaceful cabin would be a lovely place to while away a weekend. Take advantage of the nearby dock to canoe, kayak, jet ski or boat on the pristine waters. When you're done, wrap up in blankets and have a nightcap on the pretty terrace space.

The sea glass cottage in Sister Bay
Photograph: Courtesy Airbnb

9. The sea glass cottage in Sister Bay

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. 

The charming sailboat in Racine
Photograph: Courtesy Airbnb

10. The charming sailboat in Racine

If you've never spent the night on a sailboat, this is your chance. Fall asleep to the sound of lapping waves and unwind with thoughtful amenities at Reefpoint Marina, including a hot tub to soak in. The 29-foot sailboat also boasts a microwave, fridge and coffee maker aboard for a touch of land-lubbing comfort. 

The blue cottage in Mountain Beach
Photograph: Courtesy Airbnb

11. The blue cottage in Mountain 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.

The lake breeze in Lakeside
Photograph: Courtesy Airbnb

12. The lake breeze in Lakeside

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.

The lake cottage at Cypress Resort in Antioch
Photograph: Courtesy Airbnb

13. The lake cottage at Cypress Resort in Antioch

Test drive the tiny house lifestyle in this pint-sized cottage from the 1950s. The 329-square-foot home was literally sliced in half years ago to accommodate a changing lot line, creating a funky but charming studio layout. What it lacks in size it makes up for in location: The property offers 480 feet of beach access, plus a floating pier and boat launch. 

The greenwood hideaway in Union Pier
Photograph: Courtesy Airbnb

14. The greenwood hideaway in Union Pier

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.

The artist's oasis in Milwaukee
Photograph: Courtesy Airbnb

15. The artist's oasis in Milwaukee

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.

The retreat cottage in Lake Geneva
Photograph: Courtesy Airbnb

16. The retreat cottage in Lake Geneva

With an in-ground pool, outdoor fire pit and personal theater, this four-bedroom cabin certainly offers plenty of entertainment options. You’re also a short one-mile drive from Lake Geneva, where you can get your fill of sailing, paddle boarding, swimming, jet skiing and other water sports if you want to get out of the house.

The Lake Como house in Lake Geneva
Photograph: Courtesy Airbnb

17. The Lake Como house in Lake Geneva

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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