The 15 best lakeside Airbnbs for a unique getaway from Chicago

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 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 lakefront Airbnb sleeps up to six guests, so it's ideal for a family or group of friends who want a weekend trip together. You'll feel nothing but rejuvenated by the end of your vacation. 

Rooms? Two bedrooms. Sleeps two guests. 
The mood? Remixed classic cottage.  
Location perks? Prime spot for enjoying the nearby wineries and parks during your stay. 
Budget range? An up-scale family or romantic getaway. 
Time Out tip: Enjoy a spot of blueberry picking while you're here.

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. There's also a games room and seven TVS - talk about being spoiled! 

Rooms? Seven bedrooms. Sleeps up to 16 guests. 
The mood? Rustic treasure. 
Location perks? Enjoy a wealth of watersports like canoeing, kayaking and swimming. 
Budget range? An extravagant, yet affordable stay for large group bookings. 

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. 

Rooms? Two bedrooms. Sleeps three guests. 
The mood? Cosy and clean. Ahoy.  
Location perks? A walkable distance from nearby restaurants and stores. 
Budget range? An economic and blissful break for two. Have it both ways.  

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.

Rooms? One bedroom. Sleeps two.  
The mood? Rustic and homely.
Location perks? The beautiful vistas of Lake Michigan. 
Budget range? Enjoy an affordable stay in a peacful location.

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. 

Rooms? One bed. Sleeps two guests.  
The mood? Cosy cottage vibes.
Location perks? Just a short walk from all the shops, so you can Head downtown anytime you like.  
Budget range? A moderately-priced hideaway for two.

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.

Rooms? Two bedrooms. Sleep six guests. 
The mood? Heaven! 
Location perks? You'll be on the tip of Lake Michigan,  surrounded by the most spectacular views. 
Budget range? A moderately-priced retreat for a group booking.  

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.

Rooms? Three bedrooms. Sleeps six guests. 
The mood? Chic antique.
Location perks? Good travel links and cool local spots including a market, an indie bookstore and Downer Theatre.  
Budget range? A budget-friendly group booking.

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, and more!

Rooms? Four bedrooms. Sleeps 12 guests. 
The mood? Cozy-lux. 
Location perks? Gorgeous sunsets on the pier. 
Budget range? This outdoorsy family vacation home sits on the luxury end and offers affordable rates for large bookings. 
Time Out tip: Rent a pontoon, with the choice of a captain – or not.

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.

Rooms? Three bedrooms. Sleeps up to eight guests. 
The mood? Ambient lakehouse retreat.
Location perks? Enjoy Door County's shoreline on your doorstep.
Budget range? Family vacation.

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.

Rooms? Two beds. Sleeps three guests. 
The mood? Peaceful lakeside haven. 
Location perks? the ideal spot for watersports on the lake and exploring downtown Kenosha. 
Budget range? Enjoy a relaxing couple's getaway at affordable rates.

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.

Rooms? Four bedrooms. Sleep up to 10 guests. 
The mood? A lavish escape to the lake.  
Location perks? Nestled on private land close to downtown Lake Geneva. 
Budget range? A one-of-a-kind affordable luxury trip ideal for a bachelorette or bachelor do. 

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.

Rooms? Three bedrooms. Sleeps five guests. 
The mood? Charming, country-esque tiny home. 
Location perks? Beautiful sunsets over Lake Michigan. 
Budget range? This lakeside treasure is the perfect affordable stay for group bookings. 

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.

Rooms? Two bedrooms. Sleeps five guests.
The mood? A colourful and quaint private paradise.  
Location perks? Did we mention there's a private beach?!
Budget range? A dreamy week-long stay for a group of friends at a decent rate. 

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. 

Rooms? One bedroom. Sleeps two guests. 
The mood? Cosy and contemporary. 
Location perks? If you want to give wakeboarding a go, now you can. 
Budget range? Enjoy a weekend to remember at super affordable rates. 

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.

Rooms? Three bedrooms. Sleeps eight guests.
The mood? Homely and serene.
Location perks? Perfect location for exploring Geneva city and William's Bay.
Budget range? This perfect year-round family getaway is moderately priced.   
Time Out tip: To really capture the magic of Lake Como hop on a guided boat tour.