If you’re looking for cities that go all out for the holiday season, the Midwest has plenty to offer. From giant trees covered in ornaments to grand lighted displays that warm any chilly winter night, there are some fantastic Midwest vacation spots that will get even the biggest grinch in the festive holiday spirit. But bright holiday displays, fun events, and great shopping aren’t the only things to do in the Midwest this winter. The region offers plenty of beautiful scenery, a healthy mix of winter activities, and fantastic restaurants and cultural experiences.
You don’t have to look far to find Midwest vacation spots decked out in festive cheer. Depending on where you go, you may find holiday celebrations that look different than what you’re used to. Cities like Madison and Minneapolis are filled with fun activities, while towns such as Galena and Holland shine with their local traditions. Holiday concerts, tree-lighting ceremonies, and gingerbread house displays are just a few of the memorable experiences you can enjoy during your trip.
But, regardless of where you choose to visit this holiday season, you’ll find plenty of activities to enjoy, events to check out, and places to stay. Of course, Midwest getaways this holiday season aren’t all about the glitz and the glamour. There are far more things to do in the Midwest than celebrate the holidays. Your holiday getaway can include everything from visiting renowned museums to enjoying small-town charm. No matter where you go, you’ll find a warm, welcoming community celebrating the holiday season with plenty of spirit.
For an unforgettable stay, skip the big hotels and choose one of the best places to stay in the Midwest—small, independent Inns, Bed and Breakfasts, and vacation rentals. These boutique accommodations, particularly those part of the Midwest Association of Independent Inns, offer a cozy, personal experience that makes your holiday even more special. Whether you prefer a historic inn or a secluded cabin, you’ll find that these unique stays set a welcome tone for your getaway, ensuring you’ll leave these Midwest vacation spots yearning for your next visit. Join us for the holidays this year. Book one of the best places to stay in the Midwest today!
The Best Midwest Vacation Spots for the Holidays
Whether you’re planning to visit family in the Midwest this holiday season or you’re looking for a place to create one-of-a-kind memories with your closest friends and family, there are plenty of ways to ensure your time here is memorable. In fact, there are some truly fantastic Midwest vacation spots to consider visiting this season, spanning from Wisconsin and Minnesota to Iowa, Illinois, and Nebraska.
Though local cultures and traditions play a strong part in every city or town’s holiday traditions, you’ll find some commonalities in your adventures. From festive events and lighted displays to long-standing holiday traditions, these holiday destinations do a great job of capturing the joyous spirit of the Midwest. From the bright lights of Chicago to the charming streets of Stillwater, we’ve compiled a list of some of our favorite Midwest vacation spots to enjoy the magic of the season.
- Chicago is probably one of the most obvious Midwest vacation spots to enjoy this holiday season. From its European-inspired Christkindlmarket and dazzling lighted displays that will delight your inner child to the charming window displays and Macy’ and the towering Christmas tree in Millennium Park, Chicago does a fantastic job of embracing the holiday spirit.
- Just outside of Chicago, however, is another one of our favorite Midwest vacation spots for the holiday season. The historic town of Galena comes alive during the holidays with events like the Night of the Luminaria and Living Windows, where thousands of candle-lit luminaries line the streets and vibrant window displays come to (literal) life. Add to that charming historic architecture, festive decorations, and fantastic holiday shopping, and Galena is a perfect spot for a cozy yet lively holiday getaway.
- If you want small-town charm and unique holiday celebrations, head to the Amana Colonies in Iowa. The Amana Colonies offer a unique holiday experience with traditional German-style Christmas markets, carolers, and craft demonstrations. Visitors can enjoy holiday shopping, local wine tastings, and festive dining experiences in this picturesque town.
- When it comes to great Midwest vacation spots for lighted holiday displays, it’s hard to beat Omaha’s Holiday Lights Festival. The festival draws visitors from all over to see the downtown area illuminated with thousands of lights.
- Another great spot to see lit up for the holidays is the Sunken Gardens in Lincoln, Nebraska. Lincoln is also a fantastic place to do some holiday shopping, with plenty of local shops and holiday markets to explore.
- If you’d like to find laid-back Midwest vacation spots for the holidays, consider heading to Door County in Wisconsin. There, you’ll find plenty of holiday ambiance infused into the coastal charm of these communities. You can visit holiday markets and tree-lighting ceremonies and enjoy the scenery along the peninsula.
- If an urban vacation is on your mind, consider visiting Minneapolis and St. Paul. The Twin Cities offer a variety of holiday attractions, including Holidazzle in Loring Park and the European-style Christmas markets around the cities. Add in outdoor ice skating, visits to local breweries, and holiday shopping in the North Loop, and it’s easy to see why this city is a top Midwest vacation spot for the holidays.
- Venture outside the Twin Cities to nearby Stillwater, and you’ll step out of your real life and into a made-for-TV Hallmark movie. Stillwater is known for its historic charm, and during the holidays, the town’s Main Street is lined with lights. Holiday events like caroling and tree lighting make it an excellent place for a cozy, festive getaway.
- Known for its waterparks, Wisconsin Dells transforms into a winter wonderland with holiday lights and seasonal events. While the indoor waterparks stay open, visitors can also enjoy horse-drawn carriage rides, holiday shopping, and festive dinners for the perfect family-friendly holiday vacation.
- Don’t miss Christmas in historic Cedarburg, Wisconsin. It’s one of the most festive Wisconsin towns for the holidays, and their A Cedarburg Christmas event, with a packed calendar of events and activities doesn’t disappoint.
The Best Lodging in the Midwest
Though these ten Midwest vacation spots have plenty to offer, there are so many more festive destinations worth visiting across the region. You will surely find dazzling displays, joyous events, and plenty of merriment wherever you go. Elevate your holiday getaways even further when you stay at one of the independent properties associated with the Midwest Association of Independent Inns. These small inns and bed and breakfasts are often beautifully decorated for the season, filling each space with holiday charm.
Though it’s hard not to find joy when surrounded by so much holiday merriment, personalized hospitality is a hallmark of these independent inns and keeps guests coming back time and again. Our innkeepers go above and beyond to ensure every guest feels at home, offering personalized touches such as homemade holiday treats, local recommendations, and customized experiences that large hotels just can’t match. This level of attention makes each stay feel extra special, especially during the holidays.
These properties also boast cozy spaces that are perfect for enjoying the holidays. Whether you’re curling up by the fire with a good book or enjoying breakfast in a charming dining room, each inn offers a comfortable, intimate setting that allows guests to unwind and soak in the holiday spirit. Many inns even offer special holiday packages, complete with festive meals or local event tickets. Conveniently located in some of the best Midwest vacation spots, these properties provide easy access to the best of the holiday season across the Midwest. Book your holiday getaway today!
