Vacation rentals in Chicagon

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Top-rated vacation rentals in Chicagon

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Top guest favorite
Cabin in Phelps
5 out of 5 average rating, 77 reviews

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 provides stunning 360-degree views from various 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.

Top guest favorite
Home in Gaastra
4.85 out of 5 average rating, 184 reviews

"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.

Guest favorite
Home in Iron River Township
4.97 out of 5 average rating, 109 reviews

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.

Top guest favorite
Cabin in Iron River
5 out of 5 average rating, 46 reviews

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.

Guest favorite
Home in Iron River
4.87 out of 5 average rating, 30 reviews

Lakefront 3 BR Winter/Summer Wonderland (sleeps 8)

3 BR updated home on beautiful, crystal clear Chicaugon Lake. Great for all activities including listening to the Loons, swimming off of a private swim platform, 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.

Guest favorite
Cabin in Alvin
4.89 out of 5 average rating, 218 reviews

Rivers reach

Our cabin is located in the heart of the Nicolet national forest on 37.5 acres It boarders on two sides creating a beautiful and very peaceful setting. Once inside you will feel warm and comfortable while being able to see all the beauty nature has to offer through all the windows over looking the property. Plenty of space in the kitchen to prepare a meal or relax on the deck while grilling. Relax by the camp fire or cool off in the pond. Snowmobile and atv trails through back of property.

Guest favorite
Cabin in Crystal Falls
4.92 out of 5 average rating, 13 reviews

Chicagon Lake Retreat with pontoon

Relax with the whole family in Michigan’s upper peninsula on Chicagon Lake, offering 1100 acres of crystal clear water with breathtaking views of rolling hills and pines. Delightful lakefront cottage is comfortable and filled with “up north” feel. Use the pontoon for fishing adventures or leisure cruises. Your friendly dogs are welcome guests. Easy access to public launch, Young’s golf and recreational trails. Come have an unforgettable guest experience and make some lasting memories!

Guest favorite
Home in Iron River
4.95 out of 5 average rating, 96 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.

Top guest favorite
Apartment in Florence
4.94 out of 5 average rating, 185 reviews

Secluded Spread Eagle Sanctuary

Executive home lower level nestled in a private sanctuary of unique trees and shrubs. Right off ATV trail, river access with public boat launch. Extra parking for a boat, trailer, etc. Private entrance into furnished 14x24 bedroom with full bath, great room w/ 52" tv wifi, second split king size bed, fully stocked kitchen with dishes, pans, keurig, etc. dining table for 4, full stove, micro, fridge & dishwasher. Light & Airy patio doors onto lighted, covered patio with fire pit.

Top guest favorite
Home in Crystal Falls
5 out of 5 average rating, 20 reviews

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.

Guest favorite
Apartment in Gaastra
4.8 out of 5 average rating, 55 reviews

Getaway in the city of Caspian, MI

A quiet, simple 2 Bed/1 bath in the city of Caspian, MI. Several nearby lakes and river accesses. Less than a mile from the Apple Blossom trail. Nearby snowmobile/atv trails and hiking trails make this a great location for outdoor enthusiasts. Approximately 7 miles from Ski Brule and the Wisconsin border. Close to restaurants and bars including the U.P. famous Riverside Pizzeria, Kermits’s bar and Contrast Coffee. Gas/groceries close by as well.

Top guest favorite
Home in Phelps
4.95 out of 5 average rating, 154 reviews

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.

Popular amenities for Chicagon vacation rentals

  1. Airbnb
  2. United States
  3. Michigan
  4. Iron County
  5. Chicagon