Vacation rentals in Chicagon

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.

Value · Family · Skiing

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.

Family · Location · Long stay

"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.

Location · Family · Parking

Knotty Pine

Knotty Pine is a fully furnished quaint cabin located within walking distance of Stanley Lake in Iron River Michigan. This 3 bedroom cabin sleeps 6 and is small dog friendly, it offers an open concept kitchen and living room, perfect for quality family time! Knotty Pine is located within Lac O' Season's resort which offers 600 feet of sandy shore line. There is also a public boat landing just down the road. Just minutes from Ski Brule, it is also the perfect winter getaway in the Northwoods.

Location · Value · Getting around

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.

Family · Value · View

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.

Location · Family · Accuracy

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!

Family · Location · Kitchen

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.

Location · Family · Check-in

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.

Value · Location · Kitchen

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.

Location · Value · View

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.

Family · Location · View

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.

Value · Location · Nearby