Midwest Lakeside Resorts That Have Been Totally Transformed

By the age of 8, Andrew Milauckas had decided he wanted a piece of the family biz and began delivering breakfast to rooms—and taking tips—at Lake Shore Resort in Saugatuck, Michigan. Similarly, his father, Joe, recalls helping out his parents with resort chores. (Joe's friends—kids staying at Lake Shore with their families—dubbed Joseph Sr. the Job Monster.) Now, at 33, it's Andrew's turn as caretaker of the property his grandparents built nearly 70 years ago.

Joseph and Anna Milauckas left Chicago to build a getaway overlooking Lake Michigan in 1952. "The first motel rooms were chicken coops," Andrew says. He credits Grandma Anna as the ambitious visionary and entrepreneur. She wanted a motor inn-style retreat, far from a major highway. To draw travelers, Anna and Joseph plastered nearby roads with billboards: Quiet on Lake! Color TV! Heated Pool! People showed up—and they still do.

Andrew counts his parents, Joe and Donna, among the regular visitors. They arrive every morning for coffee and breakfast and to dial back some of Andrew's pricier fantasies for Lake Shore. After pursuing an advertising career in New York, Andrew returned to Saugatuck, a picturesque town tucked around the bend of Lake Michigan from Chicago. He has gradually taken the reins from his parents, and in the process, completely renovated Lake Shore. New touches include sleek mid-mod furniture, lakeside yoga classes and meditation sessions. Free bikes, kayaks and breakfast create an all-inclusive feel.

But the best parts of Lake Shore Resort haven't changed. There's the motor-lodge architecture, with low-slung buildings and private doors for every guest. ("You don't have to walk down a hall or through a lobby to the pool or the lake," Andrew says. "You just step out your door.") Sunset, a daily color show that everyone plans the day around. And familiar faces. Andrew says longtimers still refer to his grandparents by their first names, many years after they passed. But new families and young couples visit each summer too. With luck, some will still be coming back in 50 years.

Here are more classic Midwest lakeside resorts and locations that have recently been transformed into lodgings with amenities that appeal to next-gen travelers.

Quarterdeck Resort, Nisswa, Minnesota

The high-noon sun bathes Gull Lake in bright light, but these upper latitudes of Minnesota (known to those from downstate as Up North) never really get hot-hot. At Quarterdeck Resort in Nisswa, families lunch under umbrellas, and couples sidle up to an open-air bar to order Sea Breezes in their swimsuits. Beyond a narrow sandy beach lined with red Adirondack chairs, the water shimmers—clear, calm and blue as the powder-puff sky above. The only creatures in a hurry are crayfish, darting from wading feet, back to safety under the pier.

In the mid-1980s you could still find about 1,400 independent resorts fringing Minnesota's 10,000 (and then some) lakes. By some estimates, more than half have permanently shuttered. They're casualties of changing tastes and the rise of the private-home rental. But despite those challenges, Quarterdeck is booming.

Founded in 1957, the resort got a major makeover in 2018. New owners renovated the lodge suites and added several cottages and beach houses, plus a new restaurant. A 5-bedroom, 7-bath loft just opened in 2023. The goal is to appeal to 21st-century travelers who want the throwback resort feels but not the quilted polyester bed covers.

After a morning reeling in fish with house guide Walleye Dan, you'll come back to a private river-stone fireplace, crisp linens and a soothing palette of weathered blue and gray. Flexible booking acknowledges that these days, not everyone has a full week to spare. Sometimes, you just need a couple nights' escape by the water.

The Inn Hotel, Arnolds Park, Iowa

When developers demolished the Inn at Okoboji a few years ago, 120 years of history crumbled too. The property opened in 1896 and had become a fixture of the Iowa Great Lakes, a fish-hook-shape cluster of glacial pools that teems from May through September with fishermen, families and fudge-lovers. The original Inn was a little north of Arnolds Park, a beloved amusement park (and tiny municipality) on the shore of West Lake Okoboji.

The Inn Hotel, which opened a couple miles south of the old resort site, has no formal ties to the original. But the developers call it "an homage to the old," channeling the spirit of the early to mid-20th century. Palm fronds, gilded accents, and black-and-white postcards of vintage Okoboji greet guests at the front desk. Though the property is set back from the lake, with condos and green space blocking the view, guests can chill in a rooftop pool. There's also Tavern at the Park, with decor inspired by the lost world of pre-Fidel Havana—now a chic spot for a meal. And a complimentary breakfast awaits each morning in the Peacock Room.

Mission Point, Mackinac Island, Michigan

This sprawling, romantically idyllic resort on car-free Mackinac Island completed a $10 million renovation in 2019, refreshing rooms and adding a coffee shop and enhanced wellness perks. Play croquet, take a class in the cocktail garden, watch a movie in the island's only cinema, or snag an Adirondack chair on the iconic Great Lawn.

1932 Reserve, Osage Beach, Missouri

This destination's original building was the lake's oldest-known hotel, dating to 1932—just one year after the Osage River was dammed, forming Lake of the Ozarks. Now six new lofts at 1932 Reserve, including a six-bedroom penthouse, have cool details like headboards made of salvaged flooring (itself legendarily recycled from the dam's construction). The restaurant has water views and is one of the hippest spots for a meal on the lake.

Lutsen Resort, Lutsen, Minnesota

In 2018, new owners purchased one of Minnesota's largest and oldest resorts, opened in 1885. Stay affordably in a quaint, wood-paneled room in the historic lodge (pleasantly freshened up with modern linens) or book a cabin or townhouse. Amenities include a spa and restaurants, plus an impressive docket of complimentary activities, such as naturalist walks, s'mores bonfires, a nine-hole golf course and guided sea kayak trips on Lake Superior.