Vacation rentals in Chicagon

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chicagon

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1

Top guest favorite

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.

FamilyLocationSleep quality

4.99 out of 5 average rating, 160 reviews

Top guest favorite

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.

FamilyLocationHospitality

4.87 out of 5 average rating, 210 reviews

Top guest favorite

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.

Home in Iron River Township

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.

FamilyLocationBeach

4.97 out of 5 average rating, 121 reviews

Top guest favorite

The charming cabin features a vibrant red exterior with white trim accents. Surrounded by lush greenery, the entrance is marked by a covered porch area and steps leading to the door. Windows allow natural light to enter while offering a view of the wooded surroundings.

Cabin in Iron River

Knotty Pine

Knotty Pine is a fully furnished quaint cabin located within walking distance of Stanley Lake in Iron River Michigan. This 3 bedroom cabin sleeps 6 and is small dog friendly, it offers an open concept kitchen and living room, perfect for quality family time! Knotty Pine is located within Lac O' Season's resort which offers 600 feet of sandy shore line. There is also a public boat landing just down the road. Just minutes from Ski Brule, it is also the perfect winter getaway in the Northwoods.

LocationFamilyCleanliness

5.0 out of 5 average rating, 67 reviews

Top guest favorite

Home in Iron River

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.

LocationFamilyCleanliness

4.88 out of 5 average rating, 72 reviews

Guest favorite

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.

Home in Iron River

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.

FamilyLocationWifi

4.95 out of 5 average rating, 101 reviews

Guest favorite

Home in Iron River

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.

FamilyValueCondition

4.89 out of 5 average rating, 36 reviews

Top guest favorite

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.

ValueLocationAmenities

5.0 out of 5 average rating, 37 reviews

Guest favorite

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.

FamilyLocationSleep quality

4.95 out of 5 average rating, 42 reviews

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.

LocationViewParking

5.0 out of 5 average rating, 4 reviews

Top guest favorite

A spacious cabin is nestled among the trees, featuring a sturdy gray exterior and a green metal roof. Firewood is stacked neatly near the entrance, and a gravel pathway leads to the front door. A vehicle is parked nearby, indicating easy access.

Home in Town of Phelps

Phelps Seclusion

Private setting in the woods close to Phelps. Great for hunting, fishing, snowmobiling, ice fishing, skiing, and snow shoeing or just hanging out with friends and family. A full bathroom with shower. 2 bedrooms with 2 queen size bunk beds sleeps 8. Pets welcome, especially hunting dogs. A circle driveway that accommodates 2 or more boat or snowmobile trailers. We even had a trucker with a 53 foot trailer park here.

FamilyLocationAir conditioning

4.96 out of 5 average rating, 180 reviews

Guest favorite

The entrance of a log cabin is framed by tall trees, featuring a welcoming green door adorned with a decorative wreath. Two red chairs are positioned on the spacious wooden porch, offering a comfortable spot to enjoy the natural surroundings.

Cabin in Iron River

Ski Brule Log Cabin

Enjoy memorable mountain views at this lovable 3 bedroom cabin, located just a 5-minute walk from the Ski Brule lifts. Fire up the gas grill and host a cookout on the scenic back deck. Spend your nights making s’mores at the campfire pit, then cozy up inside by the wood burning stove inside while watching your favorite streaming services. A perfect cabin to gather and relax with friends and family.

LocationFamilyHiking

4.89 out of 5 average rating, 115 reviews