Vacation rentals in Chicagon

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Top-rated vacation rentals in Chicagon

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Top guest favorite
An aerial view of Wanderloft reveals its modern architectural design set against a lush green landscape. The cabin features large windows, a rooftop deck with seating, and a path leading down to the natural surroundings by Manuel Lake.
Cabin in Phelps
4.98 out of 5 average rating, 109 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.

Guest favorite
A cozy living area is presented with two comfortable sofas and an accent chair, arranged around a central coffee table. Natural light filters through the large window adorned with vertical blinds, illuminating a patterned area rug that enhances the space.
Home in Crystal Falls
4.86 out of 5 average rating, 189 reviews

Crystal Falls Cozy Pet Friendly Home

Hello! Looking for a cozy home to stay while visiting the area? Look no further! 🏡Our home is located within walking distance to downtown, grocery store, Paint River/boat landings, gas stations, snowmobile and ATV trails. Only 20 minute drive to Ski Brule. Newly remodeled kitchen, new floors, trim and paint have recently been updated. FreeWiFi & new Central Air! Use the covered back deck to relax while letting the kids play in the huge back yard/sandbox in a quiet & kid friendly neighborhood.

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
4.86 out of 5 average rating, 197 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.

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
4.97 out of 5 average rating, 115 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.

Guest favorite
Cabin in Niagara
4.91 out of 5 average rating, 55 reviews

Outdoor Paradise/Cabin - Northern Escape

Welcome to Northern Escape! Looking for a get away? Tucked away on 40 acres, this cabin is located 90 miles north of Green Bay (1 hour & 20 min drive). Only 8 min. drive from Norway, MI, & a 15 min. drive from Niagara, WI & 20 min. drive from Iron Mountain, MI. Snowmobile & ATV trails are around the corner. Fishing, Hiking, skiing & golfing are just a short drive away. Public boat launch on the Menominee river 5 miles away. Enjoy a secluded week or weekend of relaxation of full of activities.

Guest favorite
An outdoor seating area is depicted, featuring a fire pit surrounded by log stools and four chairs. A barbecue grill is positioned nearby, and a table with an umbrella is adjacent to the house, all framed by lush green trees and grass.
Cabin in Crystal Falls
4.96 out of 5 average rating, 26 reviews

Way Dam West

Up north getaway located near the west end of the Michigamme Reservoir. On recreation/snowmobile trails. Quiet, private, peaceful, easy to access. Sits on 20 acres, borders public land. Tons of wildlife including occasional moose sightings. Great deer, bear, turkey and bird hunting area. Boat launch to Way Dam less than ¼ mile from driveway. Terrific fishing, including panfish, bass, northern and walleye. Whatever your outdoor activity, this is the perfect central U.P. location.

Top guest favorite
A warm log cabin interior is highlighted, featuring natural wood paneling throughout. The kitchen area includes a gas stove and a refrigerator. A doorway leads to a bathroom with a shower, while soft lighting enhances the cozy atmosphere. A patterned runner rug adds texture to the tiled floor.
Cabin in Felch
4.98 out of 5 average rating, 127 reviews

Rustic Cabin on a Hill

Experience the great outdoors in this Newly built log cabin in the woods, 1/8 mile off of main highway. Wood and gas heat. Great get away for Honeymooners, families, couples or friends. Near snowmobile trails and secondary roads for 4 wheelers. State property next to cabin for great hunting experience. Great trout streams and fishing areas near by. One mile South of Norway Lake. Prefer nonsmokers. Check out availableity times. Thank you for looking and have a blessed day.

Guest favorite
A scenic view of Lake Ellwood is framed by large triangular windows, showcasing a vibrant sunset with orange and yellow hues reflecting on the water's surface. The wooden walls and ceiling create a cozy atmosphere, enhancing the natural beauty outside.
Cabin in Florence
4.88 out of 5 average rating, 17 reviews

Cozy cabin on the lake

Relax with the whole family at this peaceful place to stay. Located on charming Lake Ellwood in Spread Eagle, WI you will be close to everything the greater Iron Mountain, MI area has to offer including fishing, boating, hunting, snowmobiling, skiing and the famous Pine Mountain ski tournament. Relax in this cozy cabin as you enjoy the view from above Lake Ellwood or take a short ride to the Pine River boat access for a kayak ride and view of Giant Pine Mountain.

Top guest favorite
A newer cabin is set against a backdrop of lush greenery, with a gravel driveway leading to its entrance. The cabin features a two-car garage and is surrounded by well-maintained grass and trees, creating a serene outdoor environment.
Cottage in Florence
4.92 out of 5 average rating, 125 reviews

Comfortable 1 room house with private lake access.

Newer one room cabin on quiet, sparsely populated, 23 acre lake is your base for a long list of adventurous possibilities in the great north woods! Stay here & relax or enjoy the Nicolet Nat'l Forest, Spread Eagle Chain of Lakes or ski nearby! Plenty of hunting, fishing, hiking, mountain biking, opportunities in surrounding area. ATV and snowmobile trails right out the door. More than 4 in your party? Please message host, as exceptions are possible.

Guest favorite
The exterior of the timber frame cabin is showcased, featuring a rustic wood facade and a welcoming front porch. Bicycles are parked nearby, and a canoe is visible on the lawn. Surrounding trees provide a natural backdrop, with clear blue skies overhead.
Cabin in Eagle River
4.85 out of 5 average rating, 52 reviews

Sacred Place Hideaway Lake Columbus Water front

Experience refined comfort at Sacred Place Hideaway, where luxury meets nature. This private boutique retreat features elegant interiors, plush bedding, spa-style bath, fire pit lounge, scenic trails, and a fully equipped kitchen. With high-speed Wi-Fi, smart features, and peaceful surroundings, it’s perfect for rest, romance, or a quiet escape. Every detail is crafted to help you slow down, indulge, and recharge in style. Your Sacred Place Awaits!

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 Phelps
4.96 out of 5 average rating, 165 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.

Top 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
4.9 out of 5 average rating, 110 reviews

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.

Popular amenities for Chicagon vacation rentals

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