When Chicago’s lakefront and patio season is in full swing, it’s easy to stay put until cool temperatures return… but sometimes you just need to get away from city living. Plan your great—but not-so-far—escape by booking one of these five Airbnb rentals. Each one is within a five-hour drive of Chicago and gives you just what you need for easy summer living.
Driving distance from Chicago: 2.5 hours Planning a summer vacation for the entire family? Consider this beach-front property in Holland, Michigan. There’s plenty of space to spread out with six bedrooms and sprawling Macatawa Beach steps from the front door. Should you ever tire of the sand and sun, modern furnishings and panoramic lake views greet you throughout the house. Starting at $875 a night
Driving distance from Chicago: 1 hour Spend your time off in a design buff’s dream home. This modern, two-bedroom house has been featured in several design publications as part of Tryon Farm, an environmentally conscious community with 120 acres of wide-open meadows, trails, dunes, and prairies. The bright, sunny farmhouse promises to put you back in touch with nature—or at least tempt you to disconnect for a few days as you roam the property and visit nearby wineries and restaurants in New Buffalo, Lakeside, and Three Oaks. Starting at $250 a night (three night minimum)
Driving distance from Chicago: 5 hours With 300 miles of shoreline, it’s no wonder why vacationing Chicagoans flock to Wisconsin’s Door County. This charming, contemporary cottage sits way up at the northern tip of the peninsula, but it’s worth the drive, especially if you’re planning a trip with another couple. The home boasts two master suites and plenty of other bonuses: kayaks to take out on the water, bikes to ride to Ellison Bay, and paddleboards to test your balance. Starting at $350 a night
Driving distance from Chicago: 1.25 hours Summer availability at this kid-friendly home may be scarce—but there’s good reason for it. The owners put their house on Airbnb only when they’re away. Those lucky enough to score a few nights will bask in a cozy, lived-in feeling thanks to a fully-stocked kitchen and French doors that stream light into the antiquely-decorated space. Bonus: The home is nestled in the woods but is just a short walk from Warren Dunes State Park. $300 a night
Driving distance from Chicago: 1.25 hours With lake views, sleek furnishings, and space for the whole family—plus a few friends—this Michigan home has it all. It’s just steps from the shores of Lake Michigan and, if you’re willing to leave the water, a short drive to New Buffalo favorites like Oink’s Dutch Treat, The Stray Dog Bar & Grill, and Redamak’s. Starting at $800 a night