Holiday rentals in Chicagon

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Top-rated holiday rentals in Chicagon

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Top guest favourite
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, 114 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 favourite
Home in Florence
5 out of 5 average rating, 23 reviews

Remodeled/ 72"Fireplace/2 min 2 Lakes/Parks/Trails

Reconnect with your loved ones in a quiet, desirable neighborhood just 15 minutes from Iron mountain. Easy access to many surrounding lakes and waterfalls, ATV/UTV trails. Just minutes from golf & mini golf courses, go karts, antique store, ice cream shops, coffee shop & local small shops. Home offers both convenience & privacy and has been completely remodeled from top to bottom! The layout provides a great opportunity for traveling coworkers to each have their own space or families to connect

Guest favourite
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 favourite
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, 199 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 favourite
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 favourite
A charming cabin is nestled in a lush green landscape, surrounded by trees and a rocky pathway. The structure features a sloped roof and large windows, with a wind turbine visible nearby. The serene setting offers a sense of tranquility.
Cabin in Alvin
4.88 out of 5 average rating, 224 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 favourite
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
4.95 out of 5 average rating, 98 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 favourite
A wooden deck overlooks a lush landscape of green trees and a calm river. Sunlight filters through the leaves, casting gentle shadows on the deck. The railing features a modern design with wire framing, providing an unobstructed view of the serene surroundings.
Cabin in Florence
5 out of 5 average rating, 55 reviews

Little Hawaii on the river

Cozy little cabin located on the Menominee River, perfect for a weekend getaway Up North. Trail access (ATV/UTV, snowmobiles), close to the Chain of Lakes in Spread Eagle, Florence WI & Iron Mountain, MI! This cabin boasts a well-equipped kitchen, Smart TV, Wi-Fi, a fire pit for roasting s’mores, a woodstove to heat up after a cold day adventuring. Large deck with gas grill, and patio furniture with umbrella to shade during those hot summer afternoons.

Guest favourite
A spacious lake house is positioned along the water's edge, surrounded by lush greenery. A wooden dock extends into the lake, while multiple deck spaces overlook the serene water setting, enhancing the tranquil ambiance of the location.
Home in Champion
4.95 out of 5 average rating, 104 reviews

The Blue Boathouse Lake Michigamme

Enjoy a serene lake house experience on one of the Upper Peninsula’s largest inland lakes. Lake Michigamme is 4300 acres of water. Fish off the dock, watch the sunset, or lounge on one of several deck spaces. Full kitchen and grill available to fry up your catch! Wildlife neighbors include - deer, flying squirrels, bear, moose, coyotes, chipmunks, adorable backyard birds & eagles. 35 miles from Marquette Please note this is our home.

Guest favourite
A spacious bathroom is highlighted by a raised jacuzzi tub, surrounded by decorative tilework. Soft lighting fixtures and a window provide a calming ambiance. A selection of toiletries is neatly arranged nearby, enhancing the room's functional yet tranquil design.
Home in Iron Mountain
4.93 out of 5 average rating, 155 reviews

Jacuzzi Suite bungalow

Quiet and relaxing. Remodeled inside and out with spacious patio to relax in style. Pampering features include jacuzzi tub in master bedroom, body jets in bathroom shower, granite counter tops, all new furnishings and carpeting and a soothing atmosphere. Perfect to come back to after a long day at work or a romantic weekend. Our home comfortably accommodate up to 8 guests. All guests must be registered on your booking request.

Top guest favourite
The exterior of a charming house features a light blue siding with white trim and a small front porch. Three steps lead up to the front door, flanked by large windows that allow for ample natural light. Lush green grass surrounds the property.
Home in Caspian
4.9 out of 5 average rating, 116 reviews

Quiet Cute Cozy Home Close to River and ATV Trails

Kick back and relax in this calm, stylish space featuring cordless blinds, adjustable vibrating bed, on demand hot water, marble and wood floors. Fully equipped. Close to rivers, lakes, ski hills skibrule.com, paved biking/walking trail, on snowmobiling/atv trail. Quiet road, large yard. One mile from Iron River, MI.

Top guest favourite
The exterior of the retreat is shown, featuring a combination of brown wooden siding and natural stone. Large windows allow for ample light, and two wooden chairs are positioned on the gravel surface outside. Surrounding areas are decorated with autumn foliage.
Cabin in Phelps
4.81 out of 5 average rating, 197 reviews

Hussienda

For all of the outdoor enthusiasts, a four seasons retreat. A wonderful place to vacation for every season. Summer/winter vacations for relaxation, fishing, hiking, bike riding, exploring, miles of ATV trails/snowmobile trails. Beautiful fall colors for lazy strolls on miles of hiking trails, superb fishing, hunting.

Popular amenities for Chicagon holiday rentals

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