Winter doesn’t mean putting your luggage away—it means discovering a whole new side of Southwest Michigan. With frozen dunes, snow-blanketed trails, glassy Lake Michigan shores, and cozy stays, the season becomes one of adventure and relaxation. Here’s why you should plan your winter escape this year.
The lake effect delivers breathtaking winter scenery—and without the summer crowds. Locals report 60–80 inches of annual snowfall, setting the stage for a snowy wonderland. Trails, beaches, and towns glow under the winter sun.
Sledding & tubing down towering dunes at Warren Dunes State Park, where 250-foot slopes provide thrilling rides.
Cross-country skiing, snowshoeing, and fat-tire biking among the trees at parks like Love Creek County Park.
Beach walks and ice-watching along Lake Michigan’s shoreline—frozen waves, ice formations, and unspoiled views make for epic photos and peaceful reflection. Just don't climb the ice shelves and stay safe with these winter water safety tips.
South Haven Ice Rink-- Enjoy the sights and sounds of winter at this unique outdoor ice rink located in downtown South Haven. Afterward grab a cup of hot cocoa and browse the nearby shops.
Stay in one of our snug luxury homes, light the fireplace, cue a movie marathon, and let someone else handle the cooking (click here for private chef options!).
Head into town for craft beer tastings, apple cider, and rustic dinners near glowing fireplaces.
Visit heated outdoor igloos at wineries where you can sip with friends surrounded by snow-dusted vines. For winery tour recommendations, click here.
Make a splash! That's right, check out our homes in the Harbor Club (The Sandbar and SoHa Poolside Haven), which include access to an indoor pool!
Bring on the wellness with a private sound bath session from Restorative Healing Haven. Stay warm by renting a barrel sauna for your group from SoHa Saunas. Contact Bend Yoga for limited events and private classes throughout the winter.
In South Haven, explore some of these indoor activities which include museums and bowling.
From glowing light displays downtown to winter beer festivals and farmers markets, the towns of Southwest Michigan don’t hibernate—they celebrate.
November 28, 2025: Holiday in the Park -- Downtown South Haven. Snap a photo with Santa and Mrs. Claus and gather around the firepit at South Haven's annual holiday lighting ceremony. Plus enjoy a holiday parade following the trail of luminaries placed along Phoenix Street.
December 31, 2025: Ring in the New Year at the Downtown South Haven --Welcome the new year in downtown South Haven where over 1,000 beach balls will drop from the city center. Plus enjoy ice skating, features at local restaurants and shops, dancing, and adult beverages-to-go in South Haven’s Social District.
January 30-February 1, 2026: Ice Breaker Festival — Downtown South Haven. A weekend featuring ice sculptures, a chili cook-off, cardboard sled races, and more.
January 31, 2026: St. Joe Winter Beer Fest -- Downtown St. Joseph, MI. Craft beer novices and enthusiasts may enjoy sampling from local and regional Michigan breweries. *Must buy ticket for entry.
February 6-8: St. Joe Ice Fest -- Downtown St. Joseph, MI. A weekend that brings frosty fun to downtown St. Joe. Enjoy Professional Ice Carving, a Scavenger Hunt, Ice Interactives and more!
Holiday Markets & Tree Lightings — Throughout December in the region, including the Harbor Country area, with local artisan vendors and festive light displays.
Ongoing Winter Trail & Outdoor Festival Events — For winter sports, snowshoeing, and lake-shore experiences across Southwest Michigan, check here for more things to do in southwest Michigan.
Our luxury vacation homes offer the perfect base for your winter getaway: spacious, heated, stocked with amenities—and ready when you are. Whether you’re here for skiing by day and snuggling by night, or turning the weekend into a whole winter adventure, we’ve got you covered.
Don’t wait for summer to pack the bags—your winter getaway is calling. Visit Anchor Point Vacation Rentals today and find your ideal stay in Southwest Michigan. Looking for special amenities for winter? View our homes with hot tubs, firepits, or game rooms.
Let the season surprise you.
