How and Where to Responsibly Rent a Summer House Near Chicago

Can summer vacation be salvaged? Hopefully.

May 14, 2020 11:49 am
still bend schwartz house
Frank Lloyd Wright's Schwartz House in Two Rivers, WI
The Schwartz House/Airbnb

Summer in Chicagoland typically involves a road trip to some nearby Midwestern town to rent a house near some resplendent lakes, forest or meadowland. But amid fluid travel restrictions, are summer trips even viable this year?

As Illinois families entered week eight of a state-mandated stay-at-home order, it isn’t callous to think about scheduling a summer vacation, but flexibility and understanding must be prioritized if you want to turn that wishful thinking into action. The current order expires May 31, and it’s unclear what alterations will be made to it. According to Governor Pritzker, the latest modeling suggests Illinois COVID-19 cases have not peaked, and the numbers of statewide deaths are not predicted to plateau until mid-June.

Currently, nonessential travel is allowed but discouraged. Many public spaces, like beaches and parks, remain closed. It won’t be until Phase 3 of Pritzker’s plan that vacationing can be allowed in earnest, and it must follow CDC guidance. Additionally, at the moment Wisconsin and Michigan are shuttering their borders, warning Illinois residents that if they cross state lines they will need to quarantine for 14 days. Even Chicagoans with second homes are being asked to stay away.

So, can you ethically vacation this summer? Probably, but we need to establish some ground rules to be realistic about what that will look like. 

Stay isolated. Responsible vacations include ones where you are not coming into contact with other people. Stray off the beaten path in your favorite vacation towns, or venture farther out of town to discover more isolated options. Many properties are available to rent on large plots of private land, take advantage and reconnect with nature.

Prepare to cancel. Any summer travel plans need to be made with an expectation that they could be canceled. Things are changing every day under this pandemic. Be sure to understand cancellation policies and only book a trip that can be refunded. 

Be respectful. Chicago is the third largest city in the nation and was able to build a 3,000-bed field hospital in McCormick Center. Regional hospitals, on the other hand, might have five ventilators for the entire county. Do not be a burden to these medical groups. Before you travel, learn all local restrictions or government orders and abide by them. Assume the current federal power vacuum shall continue, and assume regulatory responses will be regional. 

Bring your own supplies. Don’t show up to someone else’s town and disrupt their supply chain. Try to pack as many supplies as possible to limit your shopping and interaction at your destination. 

Follow the rules. For starters, any vacation we’re talking about is going to occur in late summer, when restrictions start to relax. Repeat: we do not condone Illinoisians leaving their homes, especially for recreational vacation, until stay-at-home orders have been lifted. When we do get out, prepare to practice social distancing and wear a mask in public. If you are feeling sick, cancel the vacation and stay home. 

Keep it clean. Hotels and rental property companies have adopted new cleanliness protocols as they gear up to reopen. Marriott cites the use of hospital-grade disinfectants, Hyatt aims to implement an accreditation process from a worldwide cleaning industry association, and in May, Airbnb rolled out new cleaning protocols and mandatory waiting periods between bookings. If you want to feel more control over your vacation rental, bring your own cleaning supplies and linens.

Considering all that … planning a trip might be really good for your mental health. In an oft-cited 2010 study from the journal Applied Research in Quality of Life, researchers found participants experienced a significant increase in happiness during the planning stages of the trip. So just planning to go somewhere in August can improve your mood, regardless of if you end up going. 

To that end, we’ve compiled 13 rentals from four Midwest states to let your imagination run wild. All of them are appropriately isolated and still have late summer vacancies. All of them have a flexible cancellation policy that provides full refunds for cancellations made within 14 days of the trip. Prices are based on the same dates for each property, and are subject to change.


Via Airbnb

Mid-Century Stunner in Dundee Township, IL

Pack a nice suit and perfect your at-home cocktail making, because you’ll feel like Don Draper in this stylish mid-century modern home. Less than an hour drive from the city and set on six wooded acres, “The Alcove” is a historical landmark, a wedding venue, and now, your chance to enjoy some greenery in peace and in style.

The specs: 3 bedrooms, 4 beds, 2 baths | $215/night 

Via Airbnb

Outdoor Pool in Highland Park, IL

For the family that just needs somewhere to release their boundless, screaming children, you needn’t go far. In the North Shore enclave home to Michael Jordan’s house (still for sale if you’ve got $15 million handy), this behemoth has an outdoor pool, basketball hoop and enough lawn to create a near-regulation football or soccer field. Sign us up for Camp Quarantine. 

The specs: 6 bedrooms, 6 beds, 4 baths | $450/night  

Via Airbnb

High-End Hideaway in Ozark, IL

If you came out of the Netflix series Ozark thinking, “that seems like a nice place for a summer vacation,” by all means, have at it; but if Missouri seems a bit far off (or the show has scared you off), Illinois has its own version five hours south of the city. Expect cheerier settings than the gritty drama depicts — think Pottery Barn, not money laundering scheme gone wrong. Nestled in the woods near the waters of Shawnee Bay, this luxury home has all the creature comforts, including an outdoor hot tub. Plan a day trip to nearby Shawnee National Forest and visit The Garden of the Gods’ 320 million-year-old rock formations

The specs: 1 bedroom, 2 beds, 1 bath | $155/night

Via Airbnb

Renovated Farmhouse in Magnolia, IL

Into the idea above, but looking for a shorter drive? Just two hours southwest of Chicago (and 30 minutes drive from Starved Rock State Park) you’ll find this large, family escape. The property sits a quarter-mile from water access on Sawmill Lake, and there’s a hot tub to enjoy if lake water isn’t your thing. Knotty pine floors and meticulous farmhouse styling make this stay an aesthetically pleasing one. 

The specs: 5 bedrooms, 8 beds, 3 baths | $245/night


Via Airbnb

Chic Wooded Retreat in Michigan City, IN

Somehow simultaneously built for unplugging and daily posting to Instagram, the “Dunefarmhouse” is a modern escape situated on a former dairy farm. The property at large has five miles of trails looping through meadows, woods, prairies and ponds; however, you likely won’t be totally alone, as a collection of these unique architectural beauties dot the 170-acre expanse. 

The specs: 2 bedrooms, 4 beds, 2 baths | $275/night

Via Airbnb

Secluded Serenity in La Porte, IN

One of Airbnb’s A Plus properties (verified for quality and design), Emerson House is an elegant, expansive home perfect for the large family isolation pod. A little over an hour drive from downtown Chicago, it’s no wonder this property has been used as a wedding venue. Sitting on 30 acres of picturesque estate, a well-landscape patio leads to groomed trails and an on-property creek. Get ready to wander. 

The specs: 7 bedrooms, 7 beds, 8.5 baths | $645/night


Via Airbnb

Lakeside Tiny Home in Chetek, WI

Itching to put distance between you and the city? Buckle up for a nearly six-hour trek to upper Wisconsin, where guests will be rewarded with a tiny house on a private lake. Located in ESCAPE Village adjacent to Canoe Bay Resort, this is a bit more populated than some of the other options. If you’re willing to make the long trip and your party is adults-only, review the top-notch romantic lodging options from Canoe Bay itself.

The specs: 1 bedroom,1 bed, 1 bath | $115/night

Via Airbnb/Schwartz House

Frank Lloyd Wright’s Schwartz House in Two Rivers, WI

One of five FLWs we have our eye on, Schwartz House is a great option to stay isolated while staying active. Bikers or runners will love the access to nearby Rawley Point Trail. More than six miles of crushed-stone path skirt rivers, dunes and Lake Michigan herself, providing inspiring views. You could also spend the entire vacation simply admiring the architected views of Wright’s “Dream House,” built in 1938 for Life Magazine. 

The specs: 4 bedrooms, 4 beds, 3 baths | $450/night

Via Airbnb

Lakefront 1920s cottage in Green Lake, WI

Skip Lake Geneva and head for Green Lake, where this modernized 1920s cottage sits on the water’s edge. A stay here will break the bank, but get you as close to that All-American summer as possible, complete with cedar swing set, water-sport equipment, fire pits and sunsets over the lake — don’t forget to pack the s’mores. Things should be quiet given public gathering restrictions, but be advised next door is Grey Rock Mansion, yet another rustic wedding venue. 

The specs: 5 bedrooms, 5 beds, 3.5 baths | $1,275/night

Via Airbnb

House on a Hill in Elkhart Lake, WI

Near Sheboygan (and Kohler), this fortress sits at the crest of a 50-acre hobby farm. A perfect location for a pair of twosomes looking to hit the links at Whistling Straits, and the 3,500 square feet seem like plenty of room to socially distance, so perhaps more than one group could safely stay here together. 

The specs: 3 bedrooms, 4 beds, 3.5 baths | $320/night


Via Airbnb

Private Fishing Hole in South Haven, MI

South Haven has long been a beachside destination for Chicagoans, but the surrounding country is less heavily populated and still beautiful. A winding driveway reveals this craftsman style bungalow situated idyllically on its own fishing pond. The property extends for 20 acres, so there’s plenty of room to roam. Bring the whole family — including the dog — and wage your Pure Michigan adventure. 

The specs: 4 bedrooms, 5 beds, 2.5 baths | $600/night

Via Airbnb

Relaxing Ranch in Fennville, MI

Just inland from Saugatuck sits Fennville, and the design aesthetic of its creative, lakeside cousin has clearly been rubbing off. Modern touches are punctuated by large windows that create a treehouse view; stare off the deck into Midwestern forest that stretches for 11 private acres. While it might feel remote, this ranch is only 15 minutes drive from Saugatuck’s art and dining scene, in case things open up.

The specs: 2 bedrooms, 2 beds, 2 baths | $295/night

Via Airbnb

Private Room in Modern Fortress in Fennville, MI

Bookmark this one for the post-vaccine era since you share the space with an owner, but in the planning stage, this Fennville stunner is worth a look. A modern “cabin” in the woods, this place looks like a Mies van der Rohe was dropped from the sky. Design and nature collide but don’t clash with the enticing woodland dwelling.

The specs: 1 bedroom, 1 bed, 1 bath | $105/night


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