Holiday 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.

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.

Snowy Owl Lodge - Left Side (formerly Hot Springs)

*low tox/fragrance free-Bring the whole family to Snowy Owl Lodge—Left Side! Sleeps 12 w/ 4 bedrooms, 2 lofts, 2 full, 2 queen, 2 twin beds, futon, & 2 full baths. Enjoy the hot tub, deck, grill, firepit, laundry & plenty of space to relax. Just steps from Ski Brule, 10 mins to town, on snowmobile trail & 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.

Sauna & Pool Table: Family Home on Lake Chicagon

'Mid Summer Lodge' | Basement Bar Area | Great for Year-Round Recreation | 2,760 Sq Ft A relaxing retreat awaits you at this Iron River vacation rental! Located on Lake Chicagon, this 4-bed, 3-bath home has an open living space and a cozy basement den — perfect for friends, families, and reunions! Head to Ski Brule for a day on the slopes, explore local trails on snowmobiles, or stay home and host a pool tournament in the basement. End each day gathered for dinner and admiring the lake views.

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.

Cozy cabin in Channing, MI

Enjoy Upper Michigan's beauty in this cozy cabin in the woods. Located on 80 acres this property has over 2 miles of nature trails. Head down to Sawyer Lake just a 1/4 mile down the road. If you love to fish, you're in luck. The Michigamme river is just a few miles away. This one-bedroom cabin has a bunk room and a pull-out couch. One of my favorite features is the wood stove. It really warms you up on a chilly day. A great place to stay for a family get-away or a group of friends.

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.

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.

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.

Loon Waterfront Cottage—Menominee River

20 acres to walk/hike/XC ski around. Cozy newly renovated 2 br cottage situated on 20 acres on the banks of the scenic Menominee River with beautiful views of the river. The tranquil isolated view of the totally undeveloped far bank of the Menominee River makes one feel hundreds of miles from civilization. <work from home/WiFi <2 minutes from airport <8-10 miles from hospitals, shopping <5 minutes from Pine Mountain Ski Area

Happy Haven

This cozy 2-bedroom home has recently been remodeled. Spacious main living area. King-size in main bedroom. Full/twin bunk in 2nd bedroom. Queen-size pull-out in living room. Full bath on main floor. Centrally located in Michigan's Upper Peninsula. Close to hospital, shopping, restaurants, ATV trails, ski hill, rivers & lakes. The perfect place to navigate your northern adventures from.