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 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.

New Listing! Near Lakes & Trails, Hot Tub, Pets OK

Surrounded by forest and near some of the area’s beautiful lakes, Dawson’s Den blends rustic charm with the comforts of home. Whether you're exploring trails, relaxing in the hot tub, or unwinding in the cozy screen room, this cabin is the perfect escape. • Private hot tub • Outdoor firepit • Three-seasons screen room with cozy seating + helmet rack • Central A/C • Smart TVs + DVD library + Board games • Electric fireplace • Propane + Charcoal grill • Parking for two trailers • Kayaks included

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 - 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.

Beautiful house on Brule Lake!

Located 15 minutes west of Iron River, Michigan is a rustic getaway sure to appeal to any vacationer. Sitting in a serene setting is a beautiful home located on Brule Lake with a breathtaking view! There is a boat landing located only .5 miles down the road. This is the perfect getaway spot for you and your family to unplug, relax, and unwind. *2 Kayaks and 2 paddleboards will be available for use when staying at the property! *Fishing boat & motor boat available for rent! Msg for more info!

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.

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.

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.

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.