Vacation Rentals with Pools near Chicago

Escape out of the city and reconnect with nature at one of these inspiring vacation rentals with pools near Chicago! Within less than a couple hours' drive from The Windy City, glampers will find tranquility and luxury in a homey setting. Book a waterfront cottage on the Kalamazoo River, and you could spend your days strolling the trails or relaxing on the beach at Saugatuck Dunes State Park. Indulge in a luxurious villa surrounded by breathtaking countryside, and, when not enjoying your swimming pool and hot tub, head out to Grand Mere State Park for hiking, swimming, or kayaking in Lake Michigan. No matter where you choose to stay, these amazing rentals will tick all your boxes. See the options available near Chicago now!

No matter where you choose to stay, these amazing rentals will tick all your boxes. See the options available near Chicago now!