There’s no better time to be in the Midwest than fall. Some people prefer summer, but they conveniently forget about the mosquitoes and humidity. The one thing summer has on fall is the water: For a few brief months, it’s warm enough to wade into Lake Michigan, and those months have passed. But what if we recommended a few places that have pools and hot tubs you could use well past September 21? They exist, and they’re even better in the fall: crisp air, fall views, can’t lose.
The following rentals are all on Lake Michigan. They’re in order from the farthest north (read: Wisconsin), then south toward Chicago, and then back up the other side. The order makes a U shape. Like Lake Michigan.
Family “Retreat”
Two Rivers, Wisconsin
Have you ever been relaxing in an indoor pool in a cottage on a 15-acre property and wished there was also a hot tub on the same property? Have you ever wished there was a swordfish hanging above said pool? Wish granted! There’s also a yoga room, gym (with a Peloton), game room, outdoor fire pit and more.
Malibu House
Cleveland, Wisconsin
The listing for this six bedroom, six bathroom house includes all of the nearby activities in Sheboygan and Manitowoc — but unless you’re Gus Polinski, the Polka King of the Midwest, you’re probably not going to venture out to Sheboygan much. This house has a 45-foot indoor pool with an 85-inch TV at one end, an arcade and a movie theater. There’s also a nice gazebo with a fire pit, and Lake Michigan is literally in the backyard. Why would you leave?
Villa Santorini
Miller Beach, Indiana
You’re probably not going to find a place closer to Chicago (with views of the skyline!) on the water with a hot tub to aid in the enjoyment of viewing that skyline. This seven-bedroom house, which sleeps 16, may inspire some late-night Redfin perusal. A commute from the Loop to Miller Beach can’t be that bad, right?
Secluded Retreat
Bridman, Michigan
This four-bedroom house isn’t on the water (It’s five minutes away! The horror!) but it’s pretty much in a state park, making it a bit more desirable for the person more interested in hiking than walking on the sand. Or skip the outdoors entirely and stay inside and dive in the pool.
Modern Ecohome
Stevensville, Michigan
This one is an outlier. Yes, it has a hot tub/jet spa and it’s on Lake Michigan, but what makes it so unique is the natural pond right outside the door. It’s a freshwater pond with waterfalls, plants, rocks and boulders. The listing says it’s not a swimming pool, but guests are allowed to swim in it. This is the kind of house that might inspire your own home renovation journey. I’m envious of the pool lights alone.
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Stevensville, Michigan
Man, Stevensville seems quite modern. In addition to its proximity to Lake Michigan, this house is also near a private lake, as well as having its own pool and hot tub. Four ways to get in the water! Oh, there’s also a bathtub. Five ways.
Private Mini Resort
West Olive, Michigan
This place looks like it originated in the John Hughes cinematic universe: It’s a lovely house with a few nice touches that promise to make it a pleasant getaway for many (up to 14) people. The pool and sauna will keep you indoors, but if you need to explore, the place is on a hill over six acres. Enjoy the views.
Indoor Pool/Spa with Lake Michigan Beach Access
Norton Shores, Michigan
Water slide! This indoor pool has a water slide! It’s also a seven-bedroom house that sleeps 24 but — water slide! Who cares about bedrooms when you’re on a water slide! This place is as close as you can get to Lake Michigan without being in a boat. Good to know if you’re going for lake access. (Also: water slide!)
Sahara Oasis Retreat
Mears, Michigan
It has the prerequisite indoor pool but it’s also got a hot tub, beach access, dunes access, fire pit, fireplace and sauna. If you prefer to stay dry and sweat without huddling around a woodfire, it’s sauna time!
Blue Water’s Edge
Ludington, Michigan
Saltwater pool! What? Offering a heated saltwater pool from mid-May until Halloween, this new-build house seems like it was built explicitly for family parties and large gatherings. It sleeps 20 and also has a hot tub, outdoor shower, covered porches and multiple suites.
Lake View Bluffs
Ludington, Michigan
It’s much too cold to dive into Lake Michigan waters this time of year, especially in the northern half — but the 12-by-8-foot swim spa on top of a bluff that overlooks Lake Michigan should satisfy anyone who wants to get wet. Probably the place with the best views and no lake access on this list.
Pine Hollow in Elk Rapids
Elk Rapids, Michigan
The only bad aspect of this place is the drive time from Chicago. Nearish to Traverse City, this house offers a modern indoor pool (with a bridge?!), a kitchen worthy of a cooking competition show, a fireplace, a wood-burning pizza oven (fireplace #2?), multiple living rooms and too many custom build-outs to list. If your family is based anywhere in the Midwest or Ontario, this is the ideal home for a family reunion.
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