Travel

Cool Airbnbs Near Chicago to Book This Winter

Take a break from it all.

Courtesy of Airbnb
Courtesy of Airbnb
Courtesy of Airbnb

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. 

Courtesy of airbnb
Courtesy of airbnb
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.

Courtesy of Airbnb
Courtesy of Airbnb
Courtesy of Airbnb

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. 

Courtesy of airbnb
Courtesy of airbnb
Courtesy of airbnb

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. 

Courtesy of Airbnb
Courtesy of Airbnb
Courtesy of Airbnb

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. 

Courtesy of Airbnb
Courtesy of Airbnb
Courtesy of Airbnb

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.

Courtesy of Airbnb
Courtesy of Airbnb
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.

Courtesy of Airbnb
Courtesy of Airbnb
Courtesy of Airbnb

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.

Courtesy of Airbnb
Courtesy of Airbnb
Courtesy of Airbnb

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. 

Courtesy of Airbnb
Courtesy of Airbnb
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.

Travel

8 Suburbs Near Phoenix You Should Absolutely Visit

You could use a little space.

Discover Gilbert AZ
Discover Gilbert AZ
Discover Gilbert AZ

Phoenix is pretty great. There’s the burgeoning culinary scene, the diverse culture, the arts, of course, the sports, the great outdoors, and don’t forget about the more than 300 days of annual sunshine. We could really go on, and on, about how great this place is, but all of that greatness can blind you to all the excellence just outside it. The suburbs across The Valley are not to be missed. To encourage you to actually explore them, here’s what the best of ‘em have to offer.

Photo courtesy of Tempe Tourism
Photo courtesy of Tempe Tourism
Photo courtesy of Tempe Tourism

Tempe

Notably, Tempe is recognized as home to one of the largest universities in the country, Arizona State. But this Phoenix suburb is so much more than a college town, although it does add to its undeniable magic. Downtown Tempe plays hosts to epic arts festivals, dragon boat races, marathons and triathlons, and dozens of other events that all take place a short-distance from Tempe Town Lake, a two-mile long perennial reservoir and urban park that attracts cylicts, rowers, and active types. Break a sweat with a hike to the top of A Mountain and take in a panoramic sunset view. Or, just belly-up to the bar at one of Tempe’s innumerable craft breweries. Both are solid choices. And both can get you acquainted with this laidback Phoenix suburb.

Photo courtesy of Hotel Valley Ho
Photo courtesy of Hotel Valley Ho
Photo courtesy of Hotel Valley Ho

Scottsdale

Nearly half of Scottsdale’s land area is dedicated to open spaces and untamed desert. Outdoor activities like mountain biking, hiking, road cycling, horseback riding, and kayaking reign supreme here, and the city certainly leans toward an active, wellness-centered lifestyle. And while there’s no shortage of desert to explore, Scottsdale also claims some of the best spas in the world, award-winning restaurants, world-class golf courses, it’s the center stage for major events like luxury car auctions and sporting events, and it’s even got a bustling arts scene. This Phoenix suburb checks all of the boxes, really.

Photo by Lauren Topor Reichert
Photo by Lauren Topor Reichert
Photo by Lauren Topor Reichert

Gilbert

Not too long ago Gilbert was a sort of sleepy, far-away farm town. That’s certainly not the case anymore. Gilbert has grown exponentially, but its agricultural roots are still readily present in its personality and charm. Downtown Gilbert is home to dozens of restaurants and bars, most of which have a local, farm-to-table approach, naturally. And then there’s Agritopia, a friendly neighborhood with its very own shared garden and community spaces that include Epicenter and BARNONE, where you can order a wood-fired pizza, a can of experimental natural wine, and camp out under a canopy of trees in the open-air. It’s practically a utopia.

Mike Boening Photography
Mike Boening Photography
Mike Boening Photography

Cave Creek

A gateway to Horseshoe and Bartlett Lakes, Cave Creek’s position on the outskirts of Tonto National Forest makes it a primo spot for outdoor activities like biking and hiking and adventure by way of air balloon or horseback. Modern cowboys and gals can mosey over to The Buffalo Chip Saloon where bull riding and swing dancing are just part of a typical day. Additionally, Cave Creek has its own botanical garden, raptor rescue, and a gallery packed with person-sized crystals. And it’s all yours to discover.

Ade Russell/Flickr
Ade Russell/Flickr
Ade Russell/Flickr

Mesa

Point your GPS east and you’ll arrive in Mesa, Arizona’s third largest city. Whether you’re after outdoor adventure, looking to explore the arts and culture scene, or searching for locally made ciders and craft beer, Mesa has it all. There’s a hip, growing downtown area lined with storefronts, restaurants, theaters, and tasting rooms. And if you’re game for a little outdoor recreation, Mesa is your jumping-off point to scenic Sonoran Desert trails including Usery Mountain Regional Park, Lost Dutchman State Park, and San Tan Regional Park. Mesa is also just a short distance from The Salt River where you can cruise by wild horses and native wildlife via paddle board and Saguaro Lake is just up the road.

Experience Fountain Hills
Experience Fountain Hills
Experience Fountain Hills

Fountain Hills

At the center of this Phoenix suburb is an expansive urban park and monumental water fountain that tops out at 560-feet. The fountain in Fountain Hills is larger than the Washington Monument, and it’s three times as high as Old Faithful. Pack a picnic and spread out in the park for an afternoon where you can traverse the walkable paths, cycle around the waterway, or play a competitive bout of frisbee golf. If you swing more towards traditional golf, there’s a shortlist of premier golf courses to tee-off at. And like many of the Phoenix suburbs here, Fountain Hills is surrounded by wide-open desert and scenic vistas just waiting to be explored.

Camelback Ranch - Glendale
Camelback Ranch – Glendale
Camelback Ranch – Glendale

Glendale

Arizona sports teams including the Coyotes and Cardinals have home turf advantage in Glendale. Over the years Glendale has hosted three Super Bowl bouts and will host another in 2023. But Glendale’s not just a sports mecca for fans of professional football and hockey. This Phoenix suburb is homebase to Camelback Ranch, a modern ballpark with all the amenities where the Chicago White Sox and Los Angeles Dodgers take the field each season as part of Cactus League Spring Training. Take your time in Glendale into extra innings and visit Historic Old Town Glendale. Here you’ll encounter eclectic antique and vintage stores, restaurants, candy shops, and coffee houses.

Pedal Haus Brewery
Pedal Haus Brewery
Pedal Haus Brewery

Chandler 

Museums, urban parks, art galleries, and growing neighborhoods like Uptown Chandler and Downtown Chandler give this Phoenix suburb lots of appeal. Rows of palm trees line the Downtown area where you can start your day with a locally roasted coffee and organic breakfast bowl. Downtown Chandler regularly hosts community-focused events and it’s a popular hangout for craft beer drinkers. SanTan Brewery, Pedal Haus, and The Perch, with 40 beers on tap and tropical birds at every turn, all call this Phoenix suburb home.

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Lauren Topor Reichert is a Phoenix-based multimedia storyteller, photographer, and content creator. Her work has been featured in travel guides, national publications, and the social feeds of some stellar local restaurants. Follow her around Arizona, and beyond, on Instagram @hungryinphoenix.

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