The colder months of the year comes with a lot of excitement holidays, family get togethers, the first snowfall and getting cozy. In the midst of it all, sometimes it’s nice to have a quiet getaway and start focusing inwards. Over the past few years, I have had the privilege to experience some of the coziest stays in the Midwest. Here is our list to some of the coziest stays we have experienced. No matter what the season is, all these unique stays have their own experiences to offer anytime of the year.
Love traveling the Midwest? Here are some blog posts that feature some of the best experiences in the Midwest: List of Most Charming Towns in Minnesota, Things to Do in Traverse City, Michigan, Road Trip Itinerary for the Upper Peninsula of Michigan, Ten Adventures for Washington Island in Door County, Fun Things to Do in Bayfield, Wisconsin, Things to Do in Hot Springs, South Dakota, Family Fun Things to Do in Decorah, Iowa and Epic Adventures in Galena, IL.
1. The Anchor Inn in Traverse City, Michigan
The Anchor Inn in Traverse City, Michigan, is a charming place to stay for travelers looking to enjoy the beauty of northern Michigan and the shores of Grand Traverse Bay. With its cozy atmosphere, private beach and convenient location, it makes a great home base for exploring nearby beaches, scenic drives, local wineries, downtown Traverse City’s shops and restaurants, and the area’s many outdoor adventures. Whether you’re planning a relaxing lakeside getaway or a weekend filled with exploring, the Anchor Inn offers a welcoming place to unwind and enjoy the best of the region.
2. The Beehive in Excelsior, Minnesota
The Beehive is a charming, historic getaway in downtown Excelsior, perfect for a cozy weekend escape on the shores of Lake Minnetonka. Dating back to 1857, this beautifully restored landmark blends historic character with modern design, featuring exposed brick and stone, original wood beams, and thoughtfully decorated living spaces. The Apiary, one of the rentals in the building, offers a stylish one-bedroom retreat with a private patio and fire pit. Just a short walk away, you can explore Excelsior’s historic Water Street downtown shops, grab coffee, enjoy local restaurants, stroll along the lake, and soak up the relaxed lakeside atmosphere. It’s a wonderful place for a romantic getaway or a peaceful weekend of exploring one of Minnesota’s prettiest lake towns.
3. Thomsonite Inn on Lake Superior in Grand Marais, Minnesota
The Thomsonite Inn on Lake Superior is a charming lakeside retreat located along Minnesota’s beautiful North Shore near Grand Marais. Overlooking the sparkling waters of Lake Superior, this cozy inn offers a peaceful escape surrounded by rugged shoreline, towering trees, and breathtaking views. Guests can relax on private decks, listen to the waves, watch stunning sunrises, and explore the nearby beaches and scenic hiking trails. Its location makes it a wonderful home base for discovering North Shore highlights, including Grand Marais, Cascade River State Park, and the many waterfalls and overlooks along Highway 61. If you’re looking for a relaxing getaway filled with nature, lake views, and cozy Northwoods charm, Thomsonite Inn is a lovely place to stay.
4. Wambolts Cabins in Park Rapids, Minnesota
Wambolts Cabins in Park Rapids, Minnesota, is a historic lakeside resort that offers a classic Up North getaway surrounded by towering red pines and the peaceful waters of Upper Bottle Lake. Established in the late 1800s, this charming retreat features rustic log cabins just steps from the shoreline, creating the perfect setting for a relaxing escape into nature. Guests can spend their days swimming at the sandy beach, fishing, kayaking, canoeing, or exploring the wooded trails before unwinding on a private lakeside porch or enjoying a lakeside sauna. Guests can also choose from several cabins, both classic log style and modern shipping container. Located near Park Rapids and Itasca State Park, Wambolts is a wonderful destination for anyone looking to slow down, enjoy Minnesota’s natural beauty, and experience the timeless charm of a traditional Northwoods cabin vacation. It’s also home to the famous Headwaters of the Mississippi River.
5. Driftless Dwellings in Ferryville, Wisconsin
Driftless Dwellings in Wisconsin offers a collection of thoughtfully designed luxury cabins tucked into the beautiful Driftless Region, where rolling hills, wooded valleys, and peaceful countryside create the perfect setting for a relaxing getaway. Featuring unique vintage décor, cozy interiors, and modern comforts, these inviting retreats are ideal for a romantic weekend, a friends’ getaway, or a quiet escape into nature. Guests can unwind in a screened in hot tub, enjoy outdoor dining, relax on a screened porch, or spend evenings beneath the stars. With properties such as Aspenshire Cabin, Walnut Creek Cabin, and Cottonwood Lodge, Driftless Dwellings combines rustic charm with elevated design, making it a wonderful home base for exploring Wisconsin’s scenic backroads, charming small towns, hiking trails, and local shops.
6. The Retreat at Rosebush Creek in Grand Marais, Minnesota
The Retreat at Rosebush Creek in Grand Marais, Minnesota, is a peaceful North Shore getaway surrounded by the natural beauty of the woods and Lake Superior. It can hos tup to 8 guests, and is an inviting place to unwind, enjoy the quiet of the forest, and use as a home base for exploring the Grand Marais area. Spend your days hiking scenic trails, discovering waterfalls, visiting rocky beaches along Lake Superior, and browsing the charming shops and restaurants downtown. Whether you’re planning a relaxing weekend or an outdoor adventure, this retreat offers a wonderful way to experience Minnesota’s beautiful North Shore.
The property sits on a private eight-acre wooded lot and features a deck with treetop views of Lake Superior, a private indoor sauna, a soaking tub, a wood-burning fireplace, and a separate cabin for extra sleeping space. It’s about a 10-minute drive from downtown Grand Marais and close to Cascade River State Park and the Superior Hiking Trail. Also pet friendly!
7. Eagle Crest Cottage in Spooner, Wisconsin
Eagle Crest Cottage in Spooner, Wisconsin, is a cozy, pet-friendly lakefront getaway on beautiful Lipsett Lake, perfect for a relaxing Northwoods escape. This charming three-bedroom cabin features vaulted pine ceilings, a wood-burning fireplace, and a spacious two-tier deck with panoramic lake views. Guests can spend their days fishing, kayaking, paddle boarding, or simply enjoying the peaceful scenery before gathering around the outdoor fire pit in the evening. One of the most special features of the property is the opportunity to spot resident bald eagles nesting nearby! In winter, the area offers access to snowmobiling, ATV trails, and ice fishing. Located about 15 minutes from downtown Spooner, the cottage is also close to local coffee shops, bakeries, antique stores, and restaurants. Whether you’re planning a family vacation, a weekend with friends, or a quiet retreat with your dog, Eagle Crest Cottage offers a wonderful blend of rustic charm, lakefront relaxation, and outdoor adventure. PS: They’re pet friendly!
8. Shorely Cabin in Center City, Minnesota
Shorely Cabin in Center City, Minnesota, is a charming lakeside retreat on North Center Lake, perfect for a peaceful getaway surrounded by nature. This updated 1950s cabin combines vintage charm with modern comforts, featuring cozy bedrooms, a fully equipped kitchen, and a sunroom with beautiful lake views and a gas fireplace. Guests can enjoy the private shoreline, relax on the patio, take a kayak out on the water, or watch the sunset over the lake before gathering around the outdoor fire table. Located about an hour from the Twin Cities, Shorely Cabin is also a convenient home base for exploring nearby Taylors Falls, Interstate State Park, and the scenic Chisago Lakes area. If you want to enjoy the wineries in the rolling hills of the St. Croix River Scenic Byway, this is your stop!
9. The St. Paul Cottage in St. Paul, Minnesota
The St. Paul Cottage is less than 10 minutes from downtown St. Paul and sleep up to 8 guests. The house has a secret tree house off the trail in the woods in the backyard. We loved the balcony area – it was cozy and a great view of the stars at night. The beds are comfy, and you get a full kitchen, dining and living area to enjoy. They also updated the backyard patio to have the perfect outdoor dining experience. You can stay here and enjoy the wooded backyard with bonfires and relaxing in the hot tub, or spend a night in Minnesota’s capital city enjoying amazing restaurants, concerts, or any of the many festivals going on in the cities. We are off of the Gateway Trail, and many bike paths that lead all the way through the Twin Cities and to many of the Lakes nearby.
10. Bayfield Fruit Loop Retreat in Bayfield, Wisconsin
The Bayfield Fruit Loop Retreat is a charming Northwoods getaway tucked away on seven wooded acres just five minutes from downtown Bayfield, Wisconsin. Featuring two beautifully remodeled cottages, this peaceful retreat offers a cozy blend of rustic charm and modern comforts, with large windows overlooking the surrounding forest, inviting fireplaces, and spacious outdoor decks perfect for relaxing in nature. Gather around the firepit in the evening, enjoy a quiet morning coffee among the trees, or spend your days exploring Bayfield’s charming shops, local apple orchards, wineries, and the breathtaking shores of Lake Superior. With easy access to hiking trails, nearby state parks, the Apostle Islands, and the ferry to Madeline Island, this woodland hideaway is the perfect home base for a relaxing Wisconsin getaway filled with outdoor adventure and small-town charm.
11. Timber Bay Lodge & Houseboats in Babbitt, Minnesota
Tucked away on the beautiful shores of Birch Lake and surrounded by the towering pines of Superior National Forest, Timber Bay Lodge & Houseboats offers an unforgettable Northwoods getaway. This four-season resort combines the charm of traditional log cabins with the adventure of staying aboard a fully equipped houseboat, allowing guests to explore the lake at their own pace. Spend your days fishing for walleye, swimming in quiet coves, paddling along forested shorelines, or anchoring near a secluded island for a peaceful afternoon on the water. Back at the resort, enjoy the marina, outdoor recreation, and cozy evenings beneath the stars. Located just a short drive from Ely and the Boundary Waters region, Timber Bay is the perfect destination for anyone seeking a classic Minnesota lake vacation filled with wilderness, relaxation, and outdoor adventure.
12. The Painted Cat in Galena, Illinois
Step back in time with a stay at The Painted Cat of Galena, a charming Victorian bed and breakfast nestled inside the historic 1891 Ridd Home. This beautifully restored Queen Anne home is filled with antique furnishings, elegant architectural details, a grand staircase, cozy parlors, and a lovely library that create a truly enchanting atmosphere. What makes this bed and breakfast extra special is its resident cats, who bring plenty of personality, charm, and feline companionship to the historic home. Cat lovers will appreciate the opportunity to meet these furry residents, who add a cozy, home-like feel to the experience and make the stay even more memorable.
Guests can enjoy freshly baked pastries and coffee in the morning, relax on the inviting porches, and stroll to nearby historic Main Street to explore Galena’s boutique shops, restaurants, and historic landmarks. Perfect for a romantic weekend or a unique small-town getaway, The Painted Cat offers a memorable stay filled with Victorian elegance, warm hospitality, and plenty of kitty cuddles!
13. Lake Kosh Cabin in Fort Atkinson, Wisconsin
Escape to a cozy, dog-friendly lakeside retreat on beautiful Lake Koshkonong in Fort Atkinson, Wisconsin Lake Kosh Cabin. This inviting cabin is perfect for a relaxing getaway with your four-legged companion, offering scenic lake views, a wraparound deck, and outdoor spaces where you can unwind and enjoy the fresh air. Spend your days fishing, kayaking, swimming, or simply soaking up the peaceful atmosphere along the water. In the evenings, gather around the firepit, watch the sunset over the lake, and enjoy a quiet night away from the hustle and bustle of everyday life. With nearby waterfront restaurants and easy access to outdoor recreation, this charming Wisconsin getaway is a wonderful choice for travelers looking to enjoy lake life without leaving their furry family members behind.
14. Trimbelle Cottage in Ellsworth, Wisconsin
Escape to the peaceful countryside of western Wisconsin with a stay at The Trimbelle Cottage, a charming riverside retreat nestled on seven scenic acres in the beautiful Driftless Region. Surrounded by rolling hills, wooded areas, wildflowers, and the gentle waters of the Trimbelle River, this cozy getaway is perfect for slowing down and reconnecting with nature. Inside, enjoy a bright, welcoming home with comfortable bedrooms, a breakfast nook, and a cozy fireplace, while outside, a spacious multi-level deck features a covered hot tub, outdoor seating, and a grill.
Spend your days fishing for trout in the river, wandering the property, birdwatching, or exploring nearby small towns before gathering around the firepit beneath the stars. Dog-friendly and just about an hour from the Twin Cities, this secluded cottage is an ideal escape for couples, families, or friends looking for a relaxing Wisconsin getaway filled with rustic charm and outdoor adventure.
15. Peshtigo Pines in Crandon, Wisconsin
Escape to the Wisconsin Northwoods with a stay at The Peshtigo Pines Treehouse, a unique A-frame retreat nestled among the pine trees near the peaceful waters of Peshtigo Lake. This charming treehouse-style cabin offers a cozy, elevated hideaway where guests can unwind surrounded by nature while enjoying beautiful woodland and waterfront scenery. Perfect for couples, small families, or a quiet getaway with friends, the cabin provides a memorable alternative to a traditional vacation rental. Spend your days enjoying the lake, exploring nearby forests, fishing, or discovering the outdoor recreation opportunities throughout the Northwoods. After a day of adventure, settle in for a relaxing evening surrounded by the tranquil sights and sounds of nature. With its distinctive design and peaceful setting, Peshtigo Pines Treehouse is an inviting escape for anyone looking to unplug and experience the simple beauty of Wisconsin’s wilderness.
BONUS: The Bear Necessities in Garrison, Minnesota
This post wouldn’t be complete without also sharing The Bear Necessities, located near Mill Lacs Lakes in Garrison, Minnesota. Jennison lake is also about a ten minute walk away from the cabin. This tiny home can fit up to 4 guests and has a hot tub and outdoor movie theater. We also enjoyed the pellet fireplace in the backyard along with stargazing at night time. This cozy and charming cabin is perfect for unplugging and immersing yourself in nature with those you love most.
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