Summer may be over, but that doesn’t mean you have to stop dreaming of a getaway home. Imagine enjoying fall and winter from your second home just a few hours away from Chicago. If you don’t want (or can’t afford) a view of the lake, there are still plenty of options where you can be surrounded by nature in places like Northern Indiana, Southern Wisconsin, and Harbor Country in Michigan. Fair warning: If you’re looking for a sanctuary for rest and relaxation that’s architecturally interesting, you may have to shell out a small fortune. 

7365 W 125 N, La Porte, IN, $2,250,000

Larry Booth, a member of the postmodern Chicago Seven architects, designed this contemporary three-bedroom, two-bathroom home set on 20 acres in LaPorte, Indiana, more than 30 years ago. There is much to love about this as-is property (well, except for the high price tag). Booth thoughtfully incorporated the 4,500-square-foot structure with its surrounding environment. The window placements bring in a great deal of light and perfectly capture the tree-lined landscape. I also like the interior courtyard and saltwater lap pool. 

5965 Steele Road, Burlington, WI, $625,000

Lake Geneva and the Twin Lakes might immediately come to mind when crossing the Wisconsin border. But not far from these resort spots is a one-of-a-kind design with a cool 1970s vibe, situated on four acres outside the historic town of Burlington. Designed by a local architect for his own family, the 2,322-square-foot, three-bedroom, three-bathroom house has a lot of wood on the interior and exterior. With that outdoor pool and sprawling backyard, this looks like a great place to have a party — or just chill out.

3 Powhatan Dr, Michiana Shores, IN, $1,299,000

Here’s a storybook charmer in the beach community of Michiana Shores that was first listed for sale in mid-September. The design of the three-bedroom, three-bathroom house is a reminder of the area’s early days. It was founded by developers Orphie Gotto and Clarence Mathias who created a “log cabin town” for Chicago school teachers in the 1930s. Though an older home, the rustic look of the interior has been freshened up with white paint. I love the three-season porch that overlooks the mature trees on the property.

207 Tryon Farm Ln, Michigan City, IN, $549,000

Tryon Farm is a community of 65 modern, environmentally sensitive residences in a protected 120-acre natural area in Michigan City, Indiana. This particular country home is a little over 2,000 square feet and comes with three bedrooms and two-and-a-half bathrooms, as well as a pool. The design takes advantage of its sloped wooded lot as you can see with its variety of windows, sleeping porch, and outdoor shower. Just outside your front door are five-plus miles of walking and biking trails and more than 40 acres of open grass meadows and ponds. 

7510 Harbert Rd, Three Oaks, MI, $1,325,000

Just off the Red Arrow Highway and not far from Lake Michigan is a fantastic getaway that would be perfect as a personal residence or short-term rental. The contemporary design is spread over four levels with plenty of indoor and outdoor spaces to take in the views of the full-grown trees that surround the two-acre property. Besides the three bedrooms and three-and-a-half bathrooms, the home also comes with two screened-in porches, a yoga/exercise studio, a wine room, a deck for outdoor dining, a firepit, an inground pool, and a hot tub.