Skip to main content
Shedd Aquarium

Five Places to Stay on a Winter Getaway in Southern Illinois

Dec 17, 2024 Regional Getaways

A mother with her child dressed warmly for the weather and throwing snow in the air

Whether you’re planning a family holiday trip or a weekend getaway with friends this season, there’s no shortage of winter wonderland places to stay in Southern Illinois.

We’ve chosen five of our favorite accommodations in the Trails to Adventure region of Illinois.

Pouring a glass of rosé at a wine tasting at the Blue Sky vineyard in Illinois.

Blue Sky Vineyard

Experience a taste of Tuscany at the Blue Sky Vineyard in Makanda. More than just a winery, Blue Sky has two guest suites available for rent year round. Delicious Illinois wine and beautiful winter views of this 12-acre vineyard make for a unique and exciting experience. Venture off the property to one of the many towns dotting the Shawnee Hill Wine Trail for local meals and unique attractions.

A hot tub sitting on the deck on a cabin in the woods

Rustic Hideaway Cabins

If you’re looking for a cozy spot to enjoy a winter getaway, Rustic Hideaway Cabins might be the place for you. Each cabin includes a hot tub, fireplace and lots of privacy, making it a great option for a romantic retreat. The cabins are located in Jonesboro, close to the wine trail and other natural beauty in the region like the Pomona Land Bridge and Little Grand Canyon.

The Stablehouse

Looking for a home away from home vacation? The Stablehouse in Alto Pass is a fully-furnished, western-themed rental property that sleeps seven. Take in the serene beauty of winter this year with a close group of friends or family on this property. Pets, including horses, are welcome at this outdoor-lovers home!

An interior of a house/bedroom

Davie School Inn

Davie School Inn in Anna, near Carbondale, is on of the most unique places to stay when visiting Southern Illinois and the Shawnee Hills Wine Trail and Giant City State Park. Built in 1910, each spacious suite at the inn includes a bookcase and chalkboard from the original schoolhouse days!

A large mansion

Riverview Mansion Hotel

Golconda is home to the historic Riverview Mansion Hotel, a full service Bed & Breakfast since the 1920s. The elegant Victorian-style accommodations include a lounge serving a large selection of local wines, as well as a restaurant onsite. This enchanted hotel setting with its expansive grounds is the perfect place to enjoy the variety of Illinois wines while taking in the beautiful views of the Ohio River.

Share this story

Subscribe to Our Newsletter

Get inspired by top travel stories, gain access to exclusive promotions and contests, and discover even more reasons to #EnjoyIllinois.