10 Perfect Airbnbs for Escaping Chicago This Holiday Season

From a tiny farmhouse for two to a “family compound” that can accommodate 16

October 23, 2020 11:17 am
farmstead exterior
Could this be where you spend your next holiday?

If the thought of spending the holidays at home after nine months of being cooped up by a pandemic makes your chest tighten, it might be time to take a vacation.

“What’s a vacation in 2020?!” you scream. Well, it looks a lot like what you’re doing now, but in someone else’s house.

No matter what events are in store for your Q4 — expanding the pod for Thanksgiving dinner, trying to find a little R&R whilst breaking up the monotony, or heading to the actual hills to scream into the void — we’ve got you covered. Pack up the car, it’s time to manifest your relaxation destiny. 

Below, you’ll find 10 great Airbnbs in driving distance of Chicago (including a couple within city limits) that are perfect for the holidays, from romantic retreats for two to ample living spaces that can accommodate the whole fam-damn-ily.

Farmhouse porch
Looking for vistas? There are some here.

Tiny Farmhouse, Big Views (Fredericktown, MO)

Sleeps: 2
What you’re getting: A chic farmhouse cottage that looks like it fell out of a Pinterest spread. This one-bedroom home sits atop a valley that overlooks the owner’s farm. You’re getting a breath of fresh air, an expansive vista and 40 acres of romantic aloneness. 
Where you’re going:  Six hours south of the city, just west of Carbondale. Sit out on the porch swing and stare, drop a line in the private bass pond or take the trails and hike to your heart’s content (Mark Twain National Forest is a short drive away). The farm serves as a wedding venue, and the listing notes that “elopement services” are available, so if you’ve been waiting to reschedule your wedding, this is a pretty magical option. 

Camping by the lake
Looking to get in touch with nature?

Off the Grid, Lakeside Camping (Otter Lake, IL)

Sleeps: 4
What you’re getting: a 14×16 tent with one queen bed and plenty of cots (they say you can actually sleep up to nine). This is legit camping, as in no electricity, no wifi and no plumbing. Private, flushing outhouse, and propane heater are the most luxurious amenities. Rest assured, there’s a grocery store in town, but pack your own paperbacks, because there’s nowhere to charge the e-reader.
Where you’re going: Rent a kayak and take to the lake, or stay on land and toss some bags. Try your hand at cooking over an open flame. The point here is to slow the pace way down. 

Cottage interior
The very definition of “cozy.”

Quiet Lines = Quiet Mind (Lake Leelanau, MI)

Sleeps: 5
What you’re getting: Two bedrooms with two queen beds. This is a 100-year-old cottage that has been renovated to deliciously warm, modern levels. It’s a house devoid of clutter, so breathe easy, there are no chores to do.
Where you’re going: Take the circle tour and head north, after six hours driving through berry country, you’ll hit The Sweetbriar cottage. Plan at least one day to get blown around the 450-foot sand bluffs at Sleeping Bear Dunes. Spend the rest of your time walking to the inland Lake Leelanau, or enjoying pastoral sunsets.

Horses and trees
If your ideal of “idyllic” involves horses and trees, you’re in luck.

Farm Life at Heritage Hollow (Stockton, IL)

Sleeps: 6
What you’re getting: Two bedrooms and a queen sleeper sofa in a no-frills updated farmhouse. 
Where you’re going: If the family is looking for an interactive vacation, put ‘em to work on this secluded farm. Thirty miles south of Galena, the owners will manage interactions with horses, sheep, rabbits and chickens and can even oversee some light chores. Spend the rest of your time getting lost in 30 acres of woods, prairies and pastures.

A neatly-designed place to spend a winter’s day.

Tolman Cottage (Lake Geneva, WI)

Sleeps: 8
What you’re getting: A three bedroom, thoughtfully restored 1895 cottage. The dining room – complete with fireplace – can seat 12, so Thanksgiving is on.
Where you’re going: The point of this rental is to stay in and bask in the perfectly manufactured coziness. It’s an ideal place to wrap up with a good book. For those needing to venture out, being in a resort town certainly ensures there’s activities, and Lake Geneva has no shortage of wintertime fare: skiing, sledding, even ziplining. 

Kitchen interior
Festive holiday moods, plus a hot tub.

Hot Tubbin’ in Dune Country (Three Oaks, MI)

Sleeps: 10
What you’re getting: Three bedrooms, seven beds, outdoor hot tub and large fire pit. This open concept house — with a chef’s kitchen — makes entertaining large groups a breeze. Sure you won’t be able to use the large pool in the cold months, but there’s plenty of other outdoor space to enjoy.
Where you’re going: Ninety minutes from Chicago and just over the Indiana border, this property sits back from Cherry Beach in Three Oaks. Within a 10-minute drive, you’ll hit Greenbush Brewery and Journeyman Distillery. Expand the circle to 15 minutes and you’ll be at Warren Dunes State Park

Spacious a-frame interior
That is a magnificent fireplace.

Devil’s Lake Lodge (Devil’s Lake, WI)

Sleeps: 10
What you’re getting: Knotty pine abounds in this five-bedroom rustic lodge. The decor is woodsy, which will pair perfectly with an early winter snow, but this spot is all about the location.
Where you’re going: Three hours drive, north of Madison, sits Devil’s Lake State Park (Wisconsin’s most popular). With over 27,000 acres it shouldn’t be too hard to find some solitude. Be sure to hit up the East Bluff Trail, which includes the famed Devil’s Doorway. If hiking isn’t your thing, Tumbled Rock Brewery is walking distance from the house. Skiers and snowboarders will be pleased that Cascade Mountain is a 20-minute drive. 

Dining room table
Could this be the site of your next holiday meal?

Modern Farmhouse (Glenbeulah, WI)

Sleeps: 12
What you’re getting: Bring me your weary pod! Six smartly appointed bedrooms (with eight beds) means your large party can actually get some privacy. This rental property is outfitted for weddings and events, and it shows. They have a local, private chef they can recommend, so you don’t even have to cook your holiday meal. When nostalgia strikes, keep the fam occupied with the pool and air hockey tables.
Where you’re going: Two and a half hours north of Chicago, just west of Sheboygan. You’re a stone’s throw from Kettle Moraine State Park and its Ice Age Trail. Returning from a day of hiking, enjoy the sun set over flat pastures — it’s a great view from the firepit or the outdoor hot tub. Link up with nearby Kohler, which always has high-end events and recommendations for cross-country skiing, snowshoeing and more.

Interior design
There’s plenty of bold design to talk about here.

Multi-Generational Holiday in Lincoln Park (Chicago)

Sleeps: 14
What you’re getting: So much room for activities! This six-bedroom, 4.5-bath property is plain unruly. Part art installation, part luxury home, it seems impossible to not check a box for everyone in your extended pod with this listing. Outside is a basketball court, private deck with grill, fire pit and sectional seating (plus a table for eight). Inside there’s a sunken library room, ping-pong table, treadmill, peloton bike, three person infrared sauna and omnipresent art, color and texture. 
Where you’re going: Right in the heart of the North and Clybourn area — Boka and Alinea are your neighbors. If Chicago is a central meeting point for your extended family, this is a great option to get everyone under one roof. 

Compound interior
Looking for a spot for your large family? This might be it.

The Family Compound, City Edit (Chicago)

Sleeps: 16
What you’re getting:This six-bedroom, four-bath rental actually consists of two side-by-side penthouse units. That’s an eye-watering 5,000 square feet. For the family that needs space, if you can’t do it here — with two kitchens and two living rooms — where can you?
Where you’re going: Listen, maybe escaping your daily grind means heading into the droning traffic of the city, or not cooking a thing and eating out good with every meal — bucolic landscapes ain’t for everybody. You’ll sit a block off Randolph Street and can eat breakfast, lunch and dinner there. Experience holidays in the city from the top floor of a historic 1920s building that overlooks Fulton Market.

The InsideHook Newsletter.

News, advice and insights for the most interesting person in the room.