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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

Inn at Irish Hollow

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! 


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. Lake Michigan’s Stafford Bay 

Plush, glistening blankets of snow drape and drizzle a sentimental scene for those looking to enjoy a romantic winter getaway on the shore of Lake Michigan. Couples will find no shortage of things to do in the winter around the area. Take a guided winter rafting trip down the Sturgeon River with Big Bear Adventures. Throw on a pair of snowshoes and trek across vast, white landscapes. Warm up while shopping in Boyne City. Visit Friske Orchards ten miles south of Charlevoix. You might even enjoy taking a winter horseback ride at Boyne Highlands! 

Where to Stay 

Stafford’s Bay View Inn 

Stay in this gorgeous, Petoskey, MI mansion on the lake. Stafford’s Bay View Inn offers attentive service, country inn dining, and elegant accommodations to ensure that your stay in this relaxed, historic setting remains a pleasant memory for years to come! 

Stafford’s Bay View Inn

5. 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

Hillside Waterfront Hotel

Stay in one of the oldest buildings in Ephraim, Wisconsin. Hillside Waterfront Hotel boasts a history back to 1890 and earned its place on the National Register of Historic Places! In fact, much of the village was built around this beautiful mansion, which makes it easy for guests to explore nearby attractions. 

Hillside Waterfront Hotel

6. 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. 

Cedar Crest Lodge

Additional Romantic Winter Getaway Resources 

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.

Browse All Properties

Best Places to Stay in Canton

Gervasi Vineyard Resort & Spa
Exterior of Gervasi structure. Brick with lawn
Dining at Gervasi Vineyard
Relax at The Spa at Gervasi Vineyard
The Casa at Gervasi Vineyard Resort & Spa
still house with blue sky in the background and road in front
lake and villa
gervasi lobby
couple on lake
aerial view
luxury room
bar and sitting room
gervasi main entrance with signage against a blue background
Gervasi Vineyard marketplace
Gervasi Vineyard exterior gathering
Gervasi Vineyard exterior gathering
Gervasi Vineyard exterior

Gervasi Vineyard Resort & Spa

Canton, OH

Best Places to Stay in Ephraim

hillside night
front of hillside
two chairs
porch with charis
room with wine
guest room
front entrance
lobby of hotel
sitting room by fireplace
evening view hotel
guest room with a view
guest room
hillside dining
hillside kitchen
hillside side

Hillside Waterfront Hotel

Ephraim, WI

Best Places to Stay in Galena

aerial fall
tree changing color
guest room with fireplace
grand hall
Goldmoor Exterior at Dusk
winter Goldmoor
log cabin
guest room with fireplace
side door

Goldmoor Inn and Resort

Galena, IL

Jail Hill Inn- interior shot
Jail Hill Exterior 29
Jail Hill Inn- interior shot
Jail Hill Inn- cheese and wine
Jail Hill Room 6
Jail Hill Inn Exterior
delicious jaill hill in yogurt cup and french press coffee and tasty pastries
Jail Hill Inn- guestroom

Jail Hill Inn

Galena, IL

Best Places to Stay in Petoskey

Exterior view with lawn
chairs at lake
Front Exterior of Hotel
sitting room with fireplace
Interior Room Image
Interior sitting area
Breakfast being served

Stafford's Bay View Inn

Petoskey, MI

Best Places to Stay in Pleasanton

View of lodge and surrounding area
French Quarter Room
Couple enjoying sunset
Wood-Fired Pizza Oven
Penne Pasta with Roasted Vegetables
Elopement at Sunset
Homemade Gnocchi & Pesto
Creamy Tuscan Chicken
Breakfast Overview
Couple relaxing by one of many ponds
Caprese salad with heirloom tomatoes
Dining view in Country Meadow room
Rest and relaxation
Wood-fired pizzas right out of the oven
Fresh garden produce
Guests enjoying firepit
Foodies Package w/Artisan Cheese Board

Cedar Crest Lodge

Pleasanton, KS

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