Vacation rentals in Chicagon

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Top-rated vacation rentals in Chicagon

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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, 81 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
The exterior of the suite features a welcoming entrance adorned with flower planters overflowing with colorful blooms. A pathway leads to the door, surrounded by lush greenery and garden plants, providing a peaceful and inviting approach to the accommodation.
Guest suite in Rhinelander
4.98 out of 5 average rating, 192 reviews

Quiet Family Suite on River near Lakes and Trails

This family-size, fully-enclosed suite with a separate entrance from the host's attached house offers all the comforts of home within 15 min. of Minocqua, Rhinelander, and premier outdoor experiences- hiking, biking, fishing, boating. Inside find bright spaces, full log beams, and a hobbiton feel; open concept living area with fully stocked kitchen, table, bunk beds, large couch, TV and Wi-Fi; bedroom with queen bed and stowed air mattress; full bath; play room. The entire suite space is yours.

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
4.85 out of 5 average rating, 185 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
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
4.97 out of 5 average rating, 30 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.

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, 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.

Guest favorite
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, 219 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
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, 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.

Guest favorite
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 favorite
An aerial view captures the executive home surrounded by lush greenery and tranquil water. The spacious property features well-maintained landscaping, with the river visible in the background, framed by trees and shrubs, creating a serene and private setting.
Apartment in Florence
4.94 out of 5 average rating, 187 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
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, 22 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 favorite
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, 47 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 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
4.95 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

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