Cool Airbnbs Near Chicago to Book This Winter

Take a break from it all.

Between near-constant waves of coronavirus-related lockdowns and January’s lovely array of slushy, garbage-strewn sidewalks, there’s never been a better time to set sail for new horizons—or at least gather up your nearest and dearest and road trip it out to the perfect weekend retreat. And hey, since we’re all stuck working from home these days, you might as well tote the laptop along and make a full week out of it. Maybe even a month! What is time, anyway? 

Regardless of how long you plan to stay, we humbly present these stellar Airbnb rentals, each ready to welcome you and yours with open arms, butter soft sheets, and good old fashioned hospitality all within a four-and-a-half-hour radius of the city. 

Saugatuck Oasis
Saugatuck Oasis | Courtesy of airbnb

Saugatuck Oasis With a Heated Pool

Saugatuck, Michigan
3 bedrooms, $599 per night
Distance from Chicago: ~2.5 hours
Set on a green 1.5 acres, this charming and spacious lodge-like property is decked out to serve as the ultimate escape no matter what time of year you visit. During the warmer months, the professionally landscaped yard is a great place to kick back thanks to a breezy screened in porch, heated pool, outdoor shower, and a real-deal basketball court all to yourself. Indoors, meanwhile, a grand living room with vaulted ceilings—not to mention a towering stone fireplace—plus a gorgeous pro-grade kitchen and huge dining area are on hand to fog up the winter windows. To boot, stunning views of the nearby Kalamazoo river byways lie just a short walk (or snowshoe) away.

Calming Restful Cottage

Holland, Michigan
5 bedrooms, $325 per night
Distance from Chicago: ~2.5 hours
Set in an idyllic forested dreamscape, the term "cottage" doesn’t exactly do this joint justice considering it's essentially a picture-perfect West Elm floor display surrounded by beckoning natural elements. And even though it's mere minutes from Holland’s thriving downtown, you and your crew will likely be content staying put to sprawl about the oversized couch in front of the crackling fire, whip up meals in thein the open concept kitchen, or admire the scenery from the luxe front porch or tiered back deck. 

Waterfront 4-Story Estate on Lake Geneva

Lake Geneva, Wisconsin
6 bedrooms, $1,214 per night
Distance from Chicago: ~1.5 hours
While this place is admittedly on the pricey side, it's a remarkable waterfront home that you won’t soon forget. The contemporary four-story house is stacked with enormous windows peering out onto Lake Geneva in all its glory (the sunsets here are truly insane). You'll also get access to all of its outdoor amenities including the lakeview pool, private pier, and a spacious deck with two fully loaded BBQ grills. Inside, it's a true vacation paradise of amenities with an epic kitchen, sprawling dining table for 14, three (!!) fireplaces, a billiards table, fitness room, arcade, and, get this, a sauna. 

Frank Lloyd Wright's Schwartz House

Two Rivers, Wisconsin
4 bedrooms, $461 per night
Distance from Chicago: ~2.5 hours
Ever wanted to spend the night in a bonafide living history museum? Welcome to the Bernard Schwartz House, a perfectly preserved 1938 masterpiece designed by none other than architectural icon Frank Lloyd Wright and your new weekend crash pad. Stashed along the serene East Twin River about a mile from Lake Michigan’s crashing shores, this small town oasis is centered around an epic 63-foot-long living room featuring not one but two bricked fireplaces as well as gleaming red tidewater Cypress woodwork, expansive banquette seating, a built-in library stocked with vintage books, and all the little genius manipulations of light and space that put Wright on the map so many decades ago. The manicured yard, secluded period bedrooms, and modern kitchen swathed in exposed brick don’t hurt, either. 

The Aqua Dock on Harper Lake

Irons, Michigan
3 bedrooms, $150 per night
Distance from Chicago: ~4.5 hours
This beachside gem proves that luxury doesn’t have to come with a hefty price tag. The neatly organized cottage impresses from the jump with crisp white tongue-in-groove wood paneling broken up by industrial-style light fixtures, deep teal kitchen cabinetry, and a hulking stone fireplace buttressed with piles of freshly chopped wood. Wicker papasan chairs, a plush leather couch, and bold Persian rugs evoke a sophisticated yet cozy vibe while Turksish cotton towels, overstuffed duvets, a deep soaking tub, and wall decor straight out of an issue of Dwell provide a calming respite from all the outdoor fun lurking just beyond the broad pine plank porch. There’s even a double wide outdoor shower for warm weather... activities.

Barn of Three Oaks
Barn of Three Oaks | Courtesy of Airbnb

The Three Oaks Barn

Three Oaks, Michigan
3 bedrooms, $270 per night
Distance from Chicago: ~1.25 hours
Pack up the family, given or chosen, and make your way along Lake Michigan’s curving southern edge to find this pastoral Berrien County beauty with room for up to 11 nature-starved urbanites. Between the bare beam fireplace, dramatic arched ceiling, stately wooden dining table ringed by retro rattan chairs, and plethora of sunlight, the shabby chic vibes abound, tempered by colorful artwork and posh velvet couches and armchairs. Elsewhere, the full-sized shuffleboard table, outdoor fire pit, and sexy downstairs lounge, a warm wash of unfinished wood paneling dotted with mounted antlers and other rustic curiosities, practically beg for late night revelry. Party on, kids.

Plāhaus: A Modern Home in the Woods

Nashville, Indiana
2 bedrooms, $227 per night
Distance from Chicago: ~3.75 hours
Soak up all of Brown County’s rural riches from a strikingly urbane vantage point inside this recently remodeled vacation home. Perched atop a sweeping hill just two miles from Nashville’s main drag, this architectural beacon offers a truly unique exterior design and panoramic views that just won't quit alongside winter-geared perks like a roaring fire pit, board games galore, and a Smart TV with all the fixings if you’re the type that needs to tune in before you can fully tune out. Mid-century modern furnishings, a sleek upgraded bathroom with a rain shower, and the cheffy kitchen of your intimate dinner party dreams only add to the madness.

The Historic Owl House

Galena, Illinois
1 bedroom, $271 per night
Distance from Chicago: ~2.75 hours
A little over two and a half hours away sits the picturesque hamlet of Galena, a cherished provincial haven that’s been enchanting nose-to-the-grind Chicagoans since the Second City’s very first iteration. Get a front row seat to the small town action with a stay at this 1200-square-foot Main Street hideaway. Built around 1880, this warehouse-turned-home is equal parts slick design and antique eccentricity with a stainless steel kitchen framed in glossy black subway tile, a slate-topped butcher block gleaming beneath warm Edison bulbs, and a jet black tufted leather couch set against a backdrop of exposed brick and rugged wooden beams. Don’t miss the “rock room,” a subterranean den sporting heavy grey stone walls, a record player, and emerald green couch guaranteed to exceed all your curling-up-with-a-good-book expectations. 

Beechwood Cottage
Beechwood Cottage | Courtesy of Airbnb

Beechwood Cottage A-Frame

Sister Bay, Wisconsin
2 bedrooms, $175 per night
Distance from Chicago: ~4.5 hours
Door County has long been a top summertime destination among Midwesterners in the know but leave it to this gorgeous wooded enclave to expertly flaunt the area’s cold weather charms. Eponymous Beechwood trees cover the 1.6-acre property, providing ample privacy for the huge platform front deck and generous screened in porch. And the interior is just as lush, the soaring ceilings and two-story-tall windows giving way to tasteful mid-century furniture, plush carpeting, and an inviting potbelly stove. The lofted bedroom, nestled high in the a-frame’s cozy apex and accessible via a spiral staircase, was tailor made for the best kind of lazy Sunday mornings.

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