InsideHook Chicago Summer Rental Guide

The Summer Rental Guide

Chicago

Chicago winter: deep breath in.

Chicago summer: deep breath out. 

And we plan to make the most of this season's collective exhale outside city confines. Air's just cleaner out here.

Thusly, we present our Summer Rental Guide — a deep dive into the most desirable warm-weather haunts from Northern Michigan to Lake Geneva. 

Please enjoy. 

And we'll see you out there. 

InsideHook Chicago Summer Rental Guide

Secluded Beachfront Manse
Saugatuck, Michigan

Situated right next to Saugatuck Dunes State Park with superb views over Lake Michigan, this bananas luxury palace has everything you’ll ever need: a library, a custom La Cornue kitchen range, a master bedroom suite with a balcony, an outdoor shower and a deck that leads down to a private beach. The home’s so big it has an elevator, because of course it has an elevator. 

Book it.

InsideHook Chicago Summer Rental Guide

Marina Views
New Buffalo, Michigan

A short walk from the New Buffalo marina, this modern lakefront abode sleeps eight and offers three floors of cozy living. Floor-to-ceiling windows. Leather-tufted couches. But the real kicker: a spacious rooftop sundeck with lake views, complete with a gas fireplace should the evenings get chilly.

Book it.

InsideHook Chicago Summer Rental Guide

Geneva Lake Relaxation
Fontana, Wisconsin

An escape in Lake Geneva — an elegant manor with first and second floor decks offering jaw-dropping views of Geneva Lake. A screened-in porch perched over the waterfront will make for pleasant evenings. Relaxing whitewashed decor throughout. Plus: a private boathouse and a pier and dock. You are gonna rent a boat, right?

Book it.

InsideHook Chicago Summer Rental Guide

Romantic Beach House
St. Joseph, Michigan

At this small, modern beach shack, you’re literally just a few steps from your own private beach. No WiFi here, but no need for it — what you get instead is a well-appointed cottage complete with a viewing deck to enjoy morning coffee over the sound of the waves. Sleeps four but you’ll wanna make this getaway about you and the missus. Trust.

Book it.

InsideHook Chicago Summer Rental Guide

Scandinavian Cottage
Leelanau, Michigan

At this Scandinavian-inspired cottage in Northern Michigan, you’ll feel secluded among the wooded wilds. Inside: handsome minimalist aesthetics that complement the natural surroundings. Consider the cottage a home base to explore Northern Michigan’s harbor towns (i.e., Suttons Bay and Northport). The soaking tub is a huge plus for relaxing after a day at the property’s private beach.

Book it.

InsideHook Chicago Summer Rental Guide

Williams Bay Retreat
Williams Bay, Wisconsin

Set right at the water’s edge, this retreat in Williams Bay is all outdoor spaces with just a little kitschy twang. But you know what they say: location, location, location. A refurbished private pier with lounge chairs. And the outdoor patios offer postcard views of Geneva Lake. Just wait till the sunset hits the water.

Book it.

InsideHook Chicago Summer Rental Guide

Madeline Island Rustic
Madeline Island, Wisconsin

A ferry from the New England-ish harbor town of Bayfield gets you to Madeline Island. More specifically, it’ll get you to one of the more beautiful Wisconsin homes we’ve come across. Secluded on 18 acres amid White Pine and Birch, this home was reassembled from an 1812 barn from Vermont. They transported the wood and everything. Inside: hand-hewn beams. Viking appliances. Indoor fireplace. The island’s best explored by moped. So, you’ll wanna do that.

Book it.

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