Holiday houses in Chicagon

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Top-rated holiday rentals in Chicagon

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

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Top Guest favourite
Cabin in Phelps
4.99 out of 5 average rating, 142 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 offers stunning 360-degree views from multiple 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.

Superhost
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
4.84 out of 5 average rating, 197 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
4.87 out of 5 average rating, 204 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
The exterior of the property features a large white building surrounded by vibrant autumn trees, showcasing shades of red and orange. A manicured lawn is visible in the foreground, with a few benches arranged for outdoor seating.
Apartment in Iron River
5 out of 5 average rating, 79 reviews

Fairview School House 2 Bedroom Apartment

Formerly a schoolhouse, this beautiful property with private entrance is located just outside of Iron River, Michigan (five minutes from town) and has the best of accessibility, serenity, and privacy. Located one mile from prime snowmobile/ATV/hiking trails and access to downtown activities, grocery stores, boutique shops, thrift shops, coffeehouses, museum, lakes, fishing, and hunting. To learn more about recreation, arts, and culture in Iron County, visit Iron County Chamber of Commerce.

Superhost
Home in Crystal Falls
4.83 out of 5 average rating, 30 reviews

Deepwater Lodge Chicagon Lake! Sleeps 24!

**Pontoon and Jayco camper available** **Message us about last min summer/cancellation specials and sauna rental options****12 min to SkiBrule, direct access to trails* Huge lakehouse located on pristine, 1100 acre Chicaugon Lake. 5 bdrs + additional sleeping space, sleeps 25 and can accommodate 3-4 families. 8 min drive/5 min boat to Young's Golf Course on the lake which boasts a full restaurant/bar. Direct access to snowmobile trails/15 min drive to Ski Brule, a top Michigan ski resorts.

Guest favourite
A serene lake view is presented at sunset, with soft golden and orange hues reflecting on calm waters. Silhouetted tree lines and gentle hills are visible in the background, creating a peaceful atmosphere as clouds drift across the sky.
Cabin in Crystal Falls
4.94 out of 5 average rating, 17 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!

Top Guest favourite
A ranch-style home is set in a serene country environment, featuring a green roof and welcoming front steps. Trees surround the property, providing a sense of privacy. A gravel path leads up to the house, emphasizing the spacious outdoor area.
Home in Iron River
4.86 out of 5 average rating, 63 reviews

U. P. Hideaway llc

Relax with the whole family at this peaceful place to stay. Welcome to U P Hideaway. Enjoy this clean two bedroom one bath ranch style home located approximately six miles north of Iron River Mi. This private country setting sits on the edge of Ottawa National Forest. Enjoy nearby wildlife viewing, hiking, hunting, fishing, boating, kayaking, golfing, snowshoeing, skiing, and miles of recreational trails. Atv's , snowmobilers and equestrians are welcome. On site truck and trailer parking.

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, 100 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 favourite
Home in Iron River
4.89 out of 5 average rating, 35 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, 32 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 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
4.95 out of 5 average rating, 41 reviews

Sunset Lake - 4 Bath, Dock, Ski, UTV, Snowmobile

Escape to our cozy 3-bed, 4-bath waterfront cottage on Sunset Lake. Perfect for large groups, this year-round retreat offers stunning sunrise views, a relaxing sauna, and wood-burning fireplaces both inside and out. Enjoy two decks, a pizza oven, and direct lake access. A perfect blend of comfort and adventure for the whole family, with a dedicated workspace for remote needs. Excellent location for ski trips to Ski Brule and near trails for UTV and Snowmobile enthusiast.

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, 62 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.

Popular amenities for Chicagon holiday rentals

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