The 15 best lakeside Airbnbs for a unique getaway from Chicago

With direct beach access, a heated pool, and a cozy fire pit, this spot has outdoor relaxation covered. Inside, the basement pad offers a comfy living area, two bedrooms, two bathrooms, and a fully loaded kitchen, meaning you have everything you need for a ridiculously chill stay. And hey, if the lake and pool somehow lose their charm (unlikely), there are plenty of nearby hiking trails and X-country skiing spots nearby. Plus, it’s just a two-hour drive from Chicago. The world is your oyster at this spot.

Rooms? Two bedrooms. Sleeps up to six guests.
The mood? Beachfront bliss.
Location perks? Whether you're exploring the nearby National Park's hiking and biking trails or diving into the vibrant city life of Chicago, there's always something exciting to do while staying at this Airbnb.
Budget range? A reasonably priced option for six.

Nestled on the tranquil Grass Lake, this cozy cabin is all about relaxation. Whether you’re indulging in yard games, gathering around the bonfire, or simply soaking in those tranquil lakefront views from the deck, this spot was made for unwinding. Inside, you’ll find two comfy bedrooms, a spacious living area, and a modern kitchen space. And, to top it off, the host treats you to a selection of individually wrapped snacks and wine, all on the house. Now, that's one way to get in our good books.

Rooms? Two bedrooms. Sleeps up to five guests.
The mood? The perfect spot for a family getaway or a peaceful solo escape.
Location perks? Hike along picturesque trails, fish in pristine waters, or enjoy a refreshing swim or kayak adventure.
Budget range? A moderately-priced option, with early bird discounts available.

Looking for a property that will accommodate a large group? This beach home is the perfect choice. Its got an indoor pool, a private movie theater, and a pretty epic game room that includes a PlayStation 5, Foosball, and a pinball machine. Plus, it’s a stone’s throw away from Lake Michigan (a few steps from your backdoor) and just a short drive from the cities of Sheboygan and Manitowoc. After a busy day of adventures, you can crash in one of the property’s six bedrooms, each with its own bathroom. Trust us, this place could easily top your list of the best trips ever.

Rooms? Six bedrooms. Sleeps up to twelve guests.
The mood? Large and in charge.
Location perks? Soak in those lakeside vibes while still being only a quick 15-minute drive from Downtown Sheboygan, where you can find restaurants, markets, and shops. 
Budget range? A house this big has a price tag to match.

Fancy a motorboat included with your Airbnb? Well, at this house in Lake Como, it comes as part of the package. Though honestly, even without the speeder, this lakeside gem is a winner. Tucked away at the end of a private road, it offers tranquility in abundance. If you're up for some adventure, a fantastic hiking trail at the Hermansen Conservatory is just a few hundred yards away. And if you fancy exploring further, downtown Lake Geneva is a mere three miles away.

Rooms? Three bedrooms. Sleeps up to eight guests.
The mood? Totally chill and homey.
Location perks? This spot is perfect for discovering Geneva City and William's Bay.
Budget range? A reasonably priced stay for an all-year-round family escape.
Time Out Tip: To truly soak in the essence of Lake Como, book a guided boat tour.

To call this a ‘cabin’ might be slightly underselling the size and scope of the property. But the extensive use of wood-next-to-wood-next-to-wood throughout this unique place certainly gives it those distinct cabin vibes. It also scores highly for tranquillity points: you’ll be in a total private location on the shores of a teeny lake (not like that errm… rather bigger on nearby). It’s a paradise for outdoorsy types with the hosts providing kayaks for your use and ample opportunities for hiking and biking. Return home for creature comforts like a nice bottle of red shared on the deck or storytelling around the firepit.

Rooms? Two bedrooms. Sleeps up to four guests.
The mood? Rustic, simplified gorgeousness to bring you back to nature.
Location perks? Bird-watchers will love the views from the upper deck. Keep your eyes peeled for migratory wildfowl and other beautiful species.

Gather your friends and family for a fantastic lakeside retreat at this sprawling 5,000-square-foot lakehouse on the shores of Lake Shangrila in Bristol, Wisconsin. Sitting alongside over 200 feet of shoreline, this property offers a cozy sandy beach area, a fire pit, a grill, and a covered porch to enjoy sultry evenings. Inside, unwind in the comfort of seven bedrooms, featuring an impressive five king beds and eight twin beds. There's even a Peloton machine if you're in the mood for a workout.

Rooms? Seven bedrooms. Sleeps up to 16 guests.
The mood? Rustic treasure.
Location perks? Enjoy a ton of water activities, from canoeing and kayaking to a good ol' swim. Or, if the weather’s not on your side, kick back and relax in the home’s games room or in front of one of the seven TVs.
Budget range? An indulgent yet reasonable option for sizable group bookings.

Ever dreamt of spending a night aboard a sailboat? Well, here's your chance. Drift off to the gentle sounds of lapping waves and unwind with great amenities at Reefpoint Marina, including a relaxing hot tub. This 29-foot sailboat comes equipped with creature comforts like a microwave, fridge, and coffee maker - making it feel like a floating haven. It even has a sink with hot and cold water plus a flushing toilet, so you won't miss out on any luxuries while onboard. Plus, to keep you feeling fresh, there are convenient shower facilities less than 100 yards from the slip.

Rooms? Two bedrooms. Sleeps two guests (three in special circumstances).
The mood? Cozy and clean. Ahoy.  
Location perks? There are plenty of delicious dining spots within walking distance of the marina.
Budget range? An affordable and serene getaway for two.

This cozy one-bedroom hideout in Union Pier is just a hop away from town, where you’ll find art galleries, cute cafes, local wineries, and a well-loved public beach. But don’t worry, if you just feel like chilling on your own turf, there’s a ton to do on this plot. Whether you’re relaxing on the screened-in porch, cooking s’mores on the outdoor fire pit, or warming up in front of the wood-burning fireplace, this property guarantees zen vibes throughout your whole trip.

Rooms? One bedroom. Sleeps up to two. 
The mood? Rustic and homely.
Location perks? Sure, the interiors of this place are awesome, but those views of Lake Michigan? They’re pretty unbeatable.
Budget range? Enjoy an affordable stay in a peaceful location.

This tiny house is your ideal hub for a weekend of exploring all that Saugatuck offers. It's close to the white sands of Oval Beach, the Mount Baldhead trail, and a ton of local art galleries - seriously, the location's spot-on. Despite its size, this candy-apple red cottage packs in everything you need for a romantic getaway: a modern bathroom, queen-sized bed, kitchenette, and a screened-in porch. Plus, there's an outdoor seating area, hot tub, and gas grill - perfect for soaking up the stunning views of Lake Kalamazoo.

Rooms? One bed. Sleeps up to two guests. 
The mood? Cozy cottage vibes.
Location perks? You’re only three blocks away from downtown Saugatuck, where you’ll find shops, restaurants, and galleries. You can take a leisurely walk or hop on the two bikes provided right below the unit.
Budget range? A moderately-priced hideaway for two.

On the hunt for a serene lakefront retreat? Well, look no further. Just under a 90-minute drive from Chicago, this luxurious lakehouse is a real gem. With cozy fireplaces, a fully stocked kitchen, and sprawling decking right by the lake, it's the ultimate family escape from the city hustle. This spacious house accommodates 12 guests in four bedrooms, each with an accompanying bathroom. Spend your days swimming in the lake and return to grill up a delicious dinner - it's the perfect recipe for relaxation.

Rooms? Four bedrooms. Sleeps up to 12 guests. 
Mood? Lakeside luxury meets cozy comfort.
Location perks? Enjoy stunning sunsets from the pier.
Budget range? This high-end lakeside home offers affordable rates for larger groups.
Time Out Tip: Water sports enthusiasts will love the option to rent jet skis or canoes. Plus, the host provides a complimentary blow-up kayak.

This Door County home radiates a vintage nautical charm, with scenic views of Sturgeon Bay, maritime-themed decor, and a unique shape reminiscent of a ship's hull. Make good use of the rowboat, kayaks, and fishing gear available at the backyard pier during the day before returning home for an evening of board games while you catch mesmerizing sunsets over the water. During winter, make the most of the three sets of snowshoes provided for exploring nearby nature paths, try some ice-fishing right off the Chalet's waters, or embrace the thrill of sledding with the toboggans available at the local sled hills.

Rooms? Three bedrooms. Sleeps up to eight guests.
The mood? An ambient lakehouse retreat.
Location perks? Enjoy the beauty of Door County's shoreline right at your doorstep, along with tones of public hiking and walking trails, such as Crossroads at Big Creek.
Budget range? The perfect choice for a family vacation.

Just a short one-mile drive from Lake Geneva, this property is your gateway to sailing, paddleboarding, swimming, jet skiing, and other water adventures, offering the perfect lakeside escape. But the fun doesn't end there. The cabin boasts an in-ground pool, an outdoor fire pit, and a personal theater. Inside, you’ll enjoy the convenience of a fully equipped kitchen, three bathrooms, and a dedicated workspace (though we recommend taking a break from work - you're on holiday, after all). After a day filled with water sports, retreat to one of the four incredibly cozy bedrooms for a restful night's sleep.

Rooms? Four bedrooms. Sleeps 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. 

Test drive the tiny house lifestyle in this pint-sized 329-square-foot cottage dating back to the 1950s. The house was literally cut in half years ago to accommodate a changing lot line, creating a funky but charming studio layout. But, what it lacks in size it makes up for in location, offering 480 feet of beach access, along with a floating pier and a convenient boat launch. Explore the waters using kayaks, paddleboards, canoes, life jackets, floaties, and sand toys - all provided by the host at no additional charge. Now that's some thoughtful hosting.

Rooms? One bedroom. Sleeps up to two guests.
The mood? Cozy and contemporary.
Location perks? Nestled at the end of a quiet street, you’ll enjoy five acres of serene lakefront and an additional fifteen acres of untouched natural marsh teeming with diverse wildlife.
Budget range? Enjoy a weekend to remember at super affordable rates. 

Enjoy picture-perfect views of Lake Michigan from the huge windows of this amazing apartment. The home has recently received a makeover, so you'll have all the modern comforts for your chill lakeside retreat. Start your day with a cup of coffee, watching the sunrise paint the water in gold hues, before heading over to the city to check out popular spots like Millennium Park, Wrigley Field, and, of course, the Time Out market. After all that exploring, return home and crash in one of the three comfortable rooms while the calming sound of the waves relaxes you into a solid night's sleep.

Rooms? Three bedrooms. Sleeps up to five guests.
The mood? Ridiculously stylish with all the creature comforts.
Location perks? Enjoy a secluded lakeside retreat while staying close to the city's hustle.
Budget range? A great choice for medium-sized groups.
Time Out Tip: Make sure to grab a classic deep-dish pizza from Lou Malnati's or Giordano's if you’re in the city - we’ll let you decide your favorite.

This sunny cottage sits right on a sandy bluff with killer views of Lake Michigan. Start your day with coffee and breakfast on the patio, soaking in those gorgeous lakeside vibes, before heading down your private stairs to a long stretch of sandy paradise. Inside, there are two bedrooms, two bathrooms, a fully loaded kitchen, and a spacious living area with a massive 55-inch TV. For those looking to explore further afield, South Haven and Saugatuck are just a stone's throw away with their cute shops and quaint cafes. Trust us, this vacay will leave you feeling completely refreshed.

Rooms? Two bedrooms. Sleeps up to two guests.
The mood? A refreshed take on the classic cottage.
Location perks? Relax and unwind on a tranquil street, conveniently located near charming wineries and picturesque parks.
Budget range? An up-scale family or romantic getaway.
Time Out Tip: Don't miss the chance to enjoy some blueberry picking during your stay.