Holiday houses in Chicagon

4.99 out of 5 average rating, 159 reviews

Cabin in Town of Phelps

Lakeside Loft, Roof Deck + Sauna

Wanderloft, designed by architect David Salmela, combines modern Scandinavian design with the natural beauty of Wisconsin's Northwoods. Located on one of Vilas County's highest points, this cabin offers stunning 360-degree views from multiple levels, overlooking Manuel Lake and 9.4 acres of land. Beyond its striking design, Wanderloft is defined by its profound sense of peace and quiet - where natural beauty and thoughtful architecture create space for rest, creativity, inspiration, and renewal.

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4.87 out of 5 average rating, 210 reviews

The exterior of a single-story, white bungalow is shown, featuring a green accent at the base. Grass surrounds the home, and a ramp leads to the front entrance. Windows are visible, allowing natural light into the interior, with a fenced backyard beyond.

Home in Gaastra

"Yooper Retreat"

Cozy small-town house close to many of the activities Upper Peninsula Michigan has to offer. Time in the U.P. does not follow a clock, it is measured by your enjoyment. If you are looking for crystal palace, look elsewhere. This place offers the basic essentials in a typical Upper Peninsula small former mining community. Wi-Fi provided just in case the weather does not want to cooperate with your outdoor plans. Many of the floors recently upgraded. Bathroom updated to include shower/tub.

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Home in Iron River Township

A cozy cabin is nestled among trees, with a wooden porch facing a serene lake. The property features a gravel path leading to the home, and seasonal foliage adds splashes of color. Expansive views of the lake are visible through the trees.

3 bed/2 bath Lake House on Iron Lake - No Pet Fee.

Fisherman & outdoor enthusiasts dream place. 5 acres on Iron Lake for your family, friends, and dogs to enjoy. Ski Brule, snowmobiling, wildlife, hiking, and so many more things to enjoy. Very private. This lake is great for kayaking, canoeing,and fishing. You can swim off the dock,but there are some lily pads. The water is clear,but the bottom of the lake is mucky at shore. Great for dogs. Kayaks, canoe, & paddle boat available at your own risk. In winter, best to have AWD vehicle.

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4.97 out of 5 average rating, 121 reviews

A spacious lakefront home is set amidst lush greenery, surrounded by trees and open fields. The structure features a warm-toned exterior with a sloped roof. Clear blue skies and a hint of water are visible in the background, contributing to a serene rural atmosphere.

5.0 out of 5 average rating, 8 reviews

Lake Front Farm near Ski Brule

Peaceful Lake front Home overlooking Stanley Lake. 3 miles to Brule Mountain Ski area and Snow mobile trails. Turn of century farm includes 35 acre of property and hosts 1 large home, the original barn, cedar log cabin, lakeside sauna and dock providing access to swimming, fishing and other water sports. Main floor has screened porch, sunroom, kitchen, dining room, living room, 1 Bedroom with 1.5 baths. Lower level 3 bedrooms and 1 full bath with large rec room A one of a kind family property.

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4.88 out of 5 average rating, 72 reviews

U. P. Hideaway llc

Relax with the whole family at this peaceful place to stay. Welcome to U P Hideaway. Enjoy this clean two bedroom one bath ranch style home located approximately six miles north of Iron River Mi. This private country setting sits on the edge of Ottawa National Forest. Enjoy nearby wildlife viewing, hiking, hunting, fishing, boating, kayaking, golfing, snowshoeing, skiing, and miles of recreational trails. Atv's , snowmobilers and equestrians are welcome. On site truck and trailer parking.

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5.0 out of 5 average rating, 46 reviews

Beautiful 3-bedroom home in a rustic setting

Beautiful 3-bedroom 2 1/2 bath home that backs up to square miles of national forest property. Located across the street from Hagerman Lake in beautiful Iron County. Come to explore the U.P., hike, bike, fish, hunt, off-road, snowmobile, or just relax and enjoy the outdoors! Open floorplan design: 3 bedroom, 2.5 bath, 2 living/family rooms with smart TVs and high-speed internet access. Public boat launch within a mile. ORV trails close. Bedrooms: 1 - King 2 - Queen 3 - Twin over full

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The home features a two-story design with a wooden exterior and large glass doors. A spacious deck overlooks the water, reflecting the structure's details in the calm lake. Lush green grass surrounds the property, creating a serene outdoor setting.

4.95 out of 5 average rating, 101 reviews

The Ice House - An UPscale U.P. lake home

The Ice House is a hygge-inspired vacation home with amenities of an upscale rental. Our home is newly renovated with 100 ft of private frontage on beautiful Ice Lake. Imagine your morning cup of coffee on the master bedroom deck with panoramic views of the lake. Upscale amenities include granite countertops, 4 smart TV’s, and spa-like finishes in 3 bathrooms. The Ice House is centrally located in Iron River close to Ski Brule and other outdoor activities enjoyed in scenic Iron County.

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4.89 out of 5 average rating, 36 reviews

Lakefront 3 BR Winter/Summer Wonderland (sleeps 8)

3 BR updated home on beautiful Chicaugon Lake. Great for all activities including Loon spotting, swimming, kayaking (included), fishing from the pier or bring your own boat. Enjoy miles of ATV & snowmobile trails less than a mile down the road or hit the slopes at Ski Brule only a 30 minute drive away. Looking for inside entertainment? Test out your ping pong skills or enjoy the gaming chairs playing Nintendo Switch on the 50” Smart TV. Dock is out of water beginning October 1st.

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5.0 out of 5 average rating, 37 reviews

A comfortable living room is presented with a plush gray couch adorned with colorful throw pillows. A large television mounted on the wall displays a serene forest scene. A stylish ottoman sits in front of the couch, complementing the warm tones of the space.

Home in Crystal Falls

The Gallery House: Enjoy a Little Luxury

The Gallery House looks like an ordinary, little home in a residential neighborhood. But step inside and find exceptional amenities for your convenience, comfort, and enjoyment. Pamper yourself with the luxuries this place has to offer. Works of regional artists complement contemporary décor with a hint of mid-century style. Walk to restaurants, shops, and taverns. This in-town location is a short drive to all that this beautiful area of Michigan’s Upper Peninsula has to offer.

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4.95 out of 5 average rating, 42 reviews

A wooden deck area features a weathered table, overlooking a serene lake with calm waters reflecting the clear blue sky. Surrounding trees display autumn foliage, adding natural color to the scene. Steps lead from the deck to the lawn, enhancing outdoor accessibility.

Cottage in Iron River

Sunset Lake - 4 Bath, Dock, Ski, UTV, Snowmobile

Escape to our cozy 3-bed, 4-bath waterfront cottage on Sunset Lake. Perfect for large groups, this year-round retreat offers stunning sunrise views, a relaxing sauna, and wood-burning fireplaces both inside and out. Enjoy two decks, a pizza oven, and direct lake access. A perfect blend of comfort and adventure for the whole family, with a dedicated workspace for remote needs. Excellent location for ski trips to Ski Brule and near trails for UTV and Snowmobile enthusiast.

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Superhost

Cabin in Iron River

The Toadstool Cabin by Ursa Lodge

The Toadstool Cabin is a cozy little cabin in the woods near Stanley Lake. It offers beach access, a shared boat dock, an outdoor sauna and a hot tub. Located just down the road from the Stanley Lake boat launch and only 4 miles from the Ski Brule resort, this is the perfect destination for your year round north woods adventures. The ORV and Snowmobile trails are located just a short distance from the cabin and are accessible by local roads. Come relax with us.

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5.0 out of 5 average rating, 3 reviews