Holiday houses 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 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.

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

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.

"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.

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.

Snowy Owl Lodge - Right Side(formerly Hot Springs)

*low tox/frag free- Bring the whole family to Snowy Owl Lodge—Right Side! Sleeps 12 with 4 bedrooms, 2 lofts, 4 full beds, 2 twin beds, pull out couch, & 2 full baths. Enjoy hot tub, deck, grill, fire pit, sauna & plenty of space to relax. Just steps from Ski Brule, 10 mins to town, on snowmobile trail and near 5 lakes including Blue-Ribbon trout streams. Perfect for all seasons—ski, snowboard, snow tube, snowmobile, fish, hike, hunt, bike, waterfalls, autumn colors & more in the ❤️ of the U.P.

Peaceful 3 bedroom cabin on UTV/snowmobile trails

Watersmeet cabin on UTV/snowmobile trail L3. Property only a few hundred feet from WI/MI border and Land o Lakes WI. Open the gate and have direct access to trail system or only a short walk or bike ride to Land O Lakes. Home away from home, Spacious living, downstairs recreation room with TV, DVD player and games, extra sleeping space if needed, enclosed 3 season room, 2 outdoor patios, gas grill, 2 car attached garage for automobiles during inclement weather. Only minutes from many lakes.

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.

Grandma's House

This UP diamond in the rough is located in the old mining community of Nort' Lake; once a bustling and rustling proud community (Circa Late 1800's). Now, a quiet neighborhood ideal for bicyclist, hunters, fishing enthusiast and resting after countless adventures here in the beautiful Upper Peninsula. There are so many sites to see within miles of Grandma's House. Though this home was built in the late 1800s, you will immediately feel the warmth and comfort of a modern day living experience.

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.

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.

The base camp for your Northwoods adventure!

Enjoy the Northwoods from this centrally located vantage point. On the Pioneer Creek, you are just moments away from hunting, fishing, kayaking, cross-country skiing, snowmobiling, snowshoeing, canoeing, ATV/UTV trails, bike trails, or just plain relaxing. This carriage-house apartment can sleep up to five in a bedroom, full size hide-a-bed in living room, and loft area. Canoe is available for use.