Holiday houses in Chicagon

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chicagon

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

%{current} / %{total}1 / 1
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, 88 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
The exterior of a charming cabin is depicted, featuring a sloped roof and a welcoming porch. A large tree offers shade in the yard, surrounded by greenery and blooming flowers. A deck is accessible from the side, providing a space for outdoor relaxation.
Home in Eagle River
4.91 out of 5 average rating, 116 reviews

The Retreat Cabin on the Lake at Marmutt Woods

Our goal is rest and renewal for our guests so they return home ready to serve others and encouraged to spend regular time in prayer and God's Word. Relaxing is also a part of renewal so on-site activities and the surrounding communities offer plenty of recreation and tourism opportunities. Marmutt Woods is a place to step out of daily distractions to relax and refocus. Even if you are here primarily for some other reason, we hope you'll take advantage of the quiet time and provided materials.

Top Guest favourite
A modern living area features a wooden accent wall with a mounted television above an electric fireplace. The fireplace displays colorful illumination. A circular area rug is positioned on the floor, complementing a side table with a lamp and decorative elements, including potted plants.
Home in Florence
5 out of 5 average rating, 18 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

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, 187 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 favourite
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
4.94 out of 5 average rating, 32 reviews

Sunset Lake - Fireplace|Dock|Sauna|4 Bath|Ski|UTV

This cozy cottage is perched above a lush lakefront lawn, boasting picturesque views of Sunset Lake. Three bedrooms and four bathrooms offer space for large groups, giving you ample private and public spaces to create a memorable getaway. Play all day in any season and come back to relax by the fire or unwind in the sauna. Enjoy cooking for your crowd in the fully stocked kitchen complimented by a dining table that seats ten. Minutes from Ski Brule, state parks, town, UTV trails and local fair.

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
4.96 out of 5 average rating, 111 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 favourite
A lively dog is captured mid-leap amidst a carpet of fallen leaves, with a charming cabin nestled among colorful autumn trees. The warm wood exterior of the cabin contrasts gently with the vibrant foliage, creating a welcoming woodland setting.
Cabin in Town of Silver Cliff
5 out of 5 average rating, 210 reviews

Hardwood Hideaway Cabin on the Peshtigo River

2 Bed 1 Bath cabin. On 2 wooded acres on Peshtigo River. Private road. Walking distance to Rustic Inn-Rapids Resort-Kosirs Rafting. Parking area for trailers/boats. Well lit outdoor space. Fire pit & wood provided. 2 boat launches within a mile. WiFi/Netflix/streaming apps included. Short trail to the river. All cotton bedding and towels. 4 individual beds. Quality cookware & many kitchen supplies. Breakfast/snacks provided. Fresh eggs. Dogs are welcome with restrictions. Freshly Remodeled.

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
4.89 out of 5 average rating, 221 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
A welcoming gazebo with a circular wooden floor features a glass-top table surrounded by four cushioned chairs. Lush trees provide natural shade, while scenic views of the calm lake are visible through the surrounding railing.
Home in Iron River
4.87 out of 5 average rating, 31 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.

Top Guest favourite
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
5 out of 5 average rating, 25 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.

Top Guest favourite
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.

Top Guest favourite
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, 156 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 holiday rentals

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