Posted on November 5, 2025
The chill of winter may be approaching, but the opportunities for a getaway expands with the holiday season! Whether it's enjoying the weather or finding some cozy spots to enjoy in the warmth, there are plenty of perfect stays with events and activities for families and couples fit for the time of year. Come and take a look at our favorite homes away from the best Midwest holiday stays in Minnesota, Wisconsin, Illinois, Indiana, and Michigan.
The reaches of Boyne Mountain Resort dominate as a contender for great seasonal experiences! Shred the peaks of skis, snowboards, tubes or even their SNO-GO bikes with fast-paced action; or even the more casual snowy activities such as horseback riding, fat tiring, or the iconic SkyBridge Michigan with their Lights In The Sky event, all bringing out proper holiday magic this winter! Whether it is a calm afternoon on the slopes or evening sight seeing, you and your family are sure to have a wonderful time at Boyne Mountain Resort.
Boyne Mountain Resort (Winter Activities)
1 Boyne Mountain Rd., Boyne Falls, MI 49713 | (855) 688-7024 | Website
For a quieter stay, the picturesque Pere Marquette Lodge offers access to the wonderful attractions of the Alton region! The region's famous eagle watching experiences, festive candlelight and historical tours, and local attractions of the season await across the region! Our personal suggestions include the Loading Dock restaurant with their ice skating and live music as well as the gorgeous Grafton Winter Lights Parade! Additionally, Pere Marquette Lodge provides festive meals throughout December as well as an in-house winery, comfortable rustic rooms; and a famed indoor heated pool for all of their guests. Be sure to check out upcoming events for yourself!
Pere Marquette Lodge
13653 Lodge Blvd., Grafton, IL 62037 | (618) 786-2331 | Website
Blue Harbor Resort may be a comfortable spot to stay on Lake Michigan, but it's also host to plenty of winter fun for the whole family! For outdoor exploration, the opening of winter surfing and the annual Run Santa Run 5k are sure to be exhilarating experiences hosted near and at the Blue Harbor Resort! Additionally, the Making Spirits Bright holiday lights attraction in Sheboygan is not to be missed with a decade of luminous artwork to bring in the season!
Blue Harbor Resort
725 Blue Harbor Dr., Sheboygan, WI 53081 | (866) 701-2583 | Website
For a more personal outdoor wintery experience, check out the Grand View Lodge in Nisswa, MN! In the heart of the Northwoods, you can enjoy countless activities fit for the season. Ice fishing, tubing, skiing, snowboarding, crosscountry, evening bonfires, snowmobiling, and ice skating all await for your pick and pleasure across the selection! Additional experiences are offered for more in-house relaxation such as spa and Bingo as well if you are seeking a quieter day inside. Nevertheless, Grand View Lodge certainly is the place to be this season!
Grand View Lodge (Winter Activities)
23521 Nokomis Ave., Nisswa, MN 56468 | (866) 801-2951 | Website
The French Lick Resort closes off this list as a perfect spot for the grandeur of the holidays! From a concert with the group Lady A to the annual Christmas Carnival to the dazzling Season of Lights ceremonies the resort has plenty to offer to its guests throughout the season. What could be more ceremonious of the holiday season than spending time with friends and family in proper spirits with both colorful and courteous celebrations such as this?
French Lick Resort (Holiday Events)
8670 West State Rd. 56, French Lick, IN 47432 | (888) 936-9360 | Website