6 of the Most Magnificent Midwest Winter Getaways

The Great Lakes, rugged backcountry roads, and vast prairie land lure visitors to the Midwest each year. As temperatures drop and the snow begins to fall, the landscape transforms into a winter wonderland. Consider planning the trip of a lifetime to one of these magnificent Midwest winter getaways. Read on for some of our suggestions on where to go this winter.

“To appreciate the beauty of a snowflake it is necessary to stand out in the cold.” — Aristotle

1. Galena, IL

Attend holiday events, shop for unique gifts on Main Street, or cozy up by the fire. Galena, IL, is home to a variety of winter activities that will keep you entertained throughout the season. Fresh snow paints a scene that elicits wonder. Outdoor enthusiasts can indulge in skiing, sledding, snowshoeing, ice skating, or even ice golf!

Select Dining Suggestion: In Galena, you’ll find everything from French and German-inspired dishes to mouth-watering Italian plates. Consider eating at Fritz and Frites, Goldmoor Dining, or Fried Green Tomatoes!

Where to Stay

Jail Hill Inn

2. Ohio’s Hocking Hills

When everything freezes over in the winter, the Hocking Hills of Ohio transform into a winter wonderland. Visit wineries. Indulge in delicious cuisines. For an outdoor adventure among natural wonders, embark on a winter hike, sled at Lake Hope State Park, ice skate on Lake Logan, or go cross-country skiing at Glenlaurel Inn and Cottage!

Select Dining Suggestion: Maybe you’re in the mood for smoky BBQ. Perhaps you’re craving a sweet treat. If you find yourself in Hocking Hills, OH, consider visiting Penny’s Pastries for a donut or apple fritter. Millstone Restaurant Smoked BBQ is the place to go for wings, ribs, or pulled pork!

Where to Stay

Glenlaurel, A Scottish Inn & Cottages

Unwind in an atmosphere of effortless, old-world elegance at Glenlaurel, A Scottish Inn & Cottages. Choose between 20 inviting accommodations across a sprawling 140-acre estate. Opt for a romantic, richly-appointed room or suite to a secluded croft or cottage!

Glenlaurel

3. Ohio Wine Country

For the ultimate food and wine experience, visit Gervasi Vineyard in Canton, OH. There, you can dine at a rustic, upscale Italian Bistro, sip wine at the Crush House (a contemporary winery, wine bar, and eatery), and sample spirits at the Still House (a distillery featuring cocktails and coffee). Additionally, you learn more about their five-acre vineyard, portfolio of wines, and their state-of-the-art winemaking facilities!

Select Dining Suggestions: If you ever make it off the property to eat somewhere else, try Bender’s Tavern if you’re keeping it upscale or TD’s Tailgate Grill for a more relaxed vibe.

Where to Stay

Gervasi Vineyard Luxury Suites

If you’re going to tour the grounds and taste the wines, you might as well stay. Gervasi Vineyard’s Luxury Suites exude a Tuscan-inspired air. They offer three different ways to stay: in the Villas, in the Casa, or in the Farmhouse! Each boasts various rooms that set the scene for the ultimate getaway.

Gervasi Vineyard

4. Door County, WI

Visit quiet Door County, WI, on the peninsula between Green Bay and Lake Michigan. Here, you will encounter a diverse range of cultures and their influences from Native Americans as well as Belgian immigrants. Visit sites such as the Pioneer Schoolhouse and the Belgian Heritage Center to learn more about the region’s history. Then, spend some time gazing up at the twinkling stars beneath the cold, winter night sky in the evenings.

Select Dining Suggestions: For authentic Swedish cuisine, Al Johnson’s where goats graze atop its sod roof. You might also like to try fried cheese curds, beer cheese soup, or Colby cheese while you’re in Wisconsin!

Where to Stay

White Gull Inn

5. Pleasanton, Kansas

Known for its tranquil landscapes and warm hospitality, this quaint town offers a delightful retreat from the hustle and bustle of city life. In winter, Pleasanton transforms into a picturesque wonderland, inviting guests to explore its scenic trails, cozy up by crackling fires, and savor local flavors at charming cafes. Whether it's a peaceful weekend getaway or a chance to reconnect with nature, Pleasanton promises a rejuvenating escape where visitors can unwind and create lasting memories amidst a welcoming community that embodies warmth and genuine hospitality.

Where to Stay

Cedar Crest Lodge This 111 acre property offers breathtaking views, serene walking trails, and a tranquil outdoor pool and hot tub. The perfect place for a romantic, nature-inspired, all-inclusive getaway.

6. Hermann Missouri

Set along the Missouri River and surrounded by rolling vineyards, Hermann offers a relaxed, scenic escape rooted in wine country charm. Known for its rich German heritage, the town blends historic architecture with a welcoming, small-town atmosphere. Visitors can spend their days touring local wineries, strolling through downtown shops, or simply taking in the views of the river and surrounding hills. Whether you're visiting during harvest season or enjoying a quiet midweek retreat, Hermann invites you to slow down, savor the moment, and experience a destination defined by character, flavor, and a true sense of place.

Where to Stay

Hermann HIll Perched above the Missouri River, Hermann Hill offers a private, elevated retreat designed for rest and reconnection. Choose from luxury suites or secluded riverfront cottages, each featuring spa-like amenities, thoughtful design, and sweeping views. With in-room dining, peaceful surroundings, and an adults-only setting, it’s an ideal escape for couples looking to unwind in the heart of wine country.

Additional Romantic Winter Getaway Resources

• 6 of the Most Romantic Winter Cabin Getaways in the US
• What Are the Best Winter Honeymoon Destinations in the USA?
• Be Merry With One of the Best Christmas Vacations for Couples
• Steal a Kiss at One of These Romantic New Year’s Eve Destinations
• 6 of the Best Valentine’s Day Weekend Getaways in the US

Stay Select

Make the most of your midwest winter getaway when you stay at a Select Registry property. Cozy up in comfortable accommodations and watch the snow falling from your window. Each of our properties boasts a standard of quality that sets them apart from your standard hotel experience. Additionally, each one also exudes its own unique character. From bed and breakfasts and inns to boutique hotels and luxury lodges, rest assured that you’re in great hands.

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