Family-friendly holiday rentals in Ironwood

A charming single-family home is surrounded by lush greenery and features a combination of wood and brick exteriors. A covered porch with decorative woodwork adds character, while large windows invite light into the space. The picturesque front yard is well-maintained and complements the overall curb appeal.

4.94 out of 5 average rating, 117 reviews

Comfy Homebase for your Upper Peninsula Getaway

Centrally located 2 bed, 1.5 bath single family home all to yourself. Terrific floorplan with eat-in kitchen, large living + dining room with fireplace, 2 bedrooms and newly remodeled full bath. Powder Room on lower level. Just a few blocks to charming downtown Ironwood, Iron Belle Trail + close to Miners Park with trails for walking, mountain biking, snowshoeing, x-skiing. Quick access to all that’s amazing about the U.P.! If you love outdoor fun, this is the place to stay, relax + rejuvenate!

A welcoming living room features two comfortable sofas and an armchair arranged around a central coffee table. Soft lighting from lamps and a hanging fixture illuminates the space, while natural light filters through windows adorned with light-colored drapes. A textured area rug anchors the seating area.

4.96 out of 5 average rating, 164 reviews

Park Place - Updated Home Close to Downtown

Enjoy our freshly renovated, boho themed home near the heart of downtown Ironwood, MI featuring 2 bedrooms (1 King, 2 Queen & 1 Twin bed) & 1 bath with a beautiful soaker tub. Great starting point for any local activity. Walking, biking, ATV & snowmobile trails only a few minutes away in any direction. Self check in, but always available for help. As loving pet owners, we do allow up to 2 well-behaved dogs. Group event? Book the house next door too (up to 13 guests): airbnb.com/h/greenhaveniwd

4.97 out of 5 average rating, 101 reviews

A scenic winter landscape features a gently sloping hill covered in fresh snow, marked with ski tracks. Trees with bare branches frame the scene, leading up to a cozy building nestled among the trees, accented by a clear blue sky overhead.

Apartment in Wakefield

Cute & Cozy 1B/1B Condo w/ Jetted Tub!

My clean, cozy, quiet, and Completely remodeled condo is located at Indianhead/Snowriver Resort. It's a brief walk to the Sky Bar/Jack's Cafe on site for food, drink, and the best views from the top of the ski hill in the Upper Peninsula. My condo is the perfect place for your romantic getaway, family trip, after hiking/camping refresh, ski vacation, or peace and quiet on the mountaintop. I provide exceptional communication and top notch responsiveness. You won't be disappointed with your stay!

4.95 out of 5 average rating, 130 reviews

The entrance features a white door adorned with a festive wreath and flanked by windows. A large 'WELCOME' sign, decorative greenery, and a small chair are positioned on the porch, creating an inviting entryway.

Bungalow in Ironwood

HOT FIND *Powderhorn Porch* 4B/1BA dwntwn Bungalow

Welcome to the Powderhorn Porch! When you get off the trails or slopes there isn't a better place to come home to than this cozy 4BR/1BA bungalow located in downtown Ironwood just blocks from the trails. Long driveway to hold your vehicles and trailers. Centrally located to all that the Gogebic Range has to offer including 4 ski resorts, snowmobile trails, waterfalls, hiking, Porkies, Lake Superior, Copper Peak, and cute shops & restaurants. This home is perfect for your next trip to the UP!

4.8 out of 5 average rating, 378 reviews

A studio space features a spacious bed and a queen sofa sleeper, accented by neutral-colored walls. Natural light enters through a nearby window, illuminating the cozy sitting area with its black couch. A small dining table and kitchenette are seen in the background.

Apartment in Bayfield

One Minute Walk to Lake Superior. Brookside #11

Amazing location! This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. Strong Wifi, balcony, AC, CableTV and fire pit wood provided. 1 minute walk to the marina. Bayfield is 2.3 mi from Brookside. Hike or bike the Brownstone trail along the lake. Take the ferry to Madeline, cruise the apostles, Sail, fish, kayak, golf, orchards, ski and more!! The pool and restraunt opens July 1st. 5 minutes from Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

The exterior of the house features a light green facade with white trim and a welcoming front porch. A swing chair and two wooden chairs provide seating, while a small set of stairs leads to the entrance. Lush greenery surrounds the base of the house.

4.96 out of 5 average rating, 272 reviews

The House Next Door, In-Town Two Story House

The House Next Door has a Northwoods feel while being in town and close to your likely destination. Just four blocks from downtown Ironwood, and in the heart of all the outdoor adventure the Gogebic Range has to offer. You'll love the warm cozy feel, and the ability to mingle in the open concept lr/dr/kitchen downstairs, or retreat upstairs for a quiet, peaceful setting. Individuals, couples, families, and up to eight friends would enjoy my place, provided you can live with one bathroom.

4.97 out of 5 average rating, 263 reviews

A sitting area features a futon draped with a cozy blanket, complemented by colorful accent pillows. A spacious bed with a patterned coverlet is positioned nearby, while a countertop with bar stools creates an inviting space for dining or gathering.

Tiny home in Saxon

Parker Creek Tiny House

Come stay on our hobby farm with us! We are in a great central location to multiple hiking trails and gorgeous falls. We have had many guests visit the sea caves in Cornucopia, spend the day in Bayfield, or hike the Porcupine Mountains. We also are only a few miles from the ATV trails if you would rather spend the day riding the trails. We have multiple places to mountain bike or kayak. We have more things to do listed in our details section! Feel free to message me with questions.

Campervan/Motorhome in Ironwood

A cozy trailer, nestled among leafy greenery and trees, features a rustic exterior with wood accents. The entrance is framed by bushes and wild plants, creating a sense of seclusion in the tranquil forest setting.

4.92 out of 5 average rating, 159 reviews

Off grid Shasta trailer at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Sodalite Shasta with opportunities for hiking, biking, swimming, boating and everything in between. This off grid, cozy 14' trailer is situated on a two acre lot with two other rentals and my full time residence on the edge of the Ottawa National Forest. A short walk to Black River Harbor, the North Country Trail & Lake Superior, this is a perfect getaway for those seeking a rustic yet comfortable stay with a campy feel.

4.95 out of 5 average rating, 274 reviews

A charming A-frame chalet is surrounded by vibrant autumn foliage. The exterior features a blue metal roof and large windows that allow natural light to fill the interior. A wooden deck extends from the front, providing outdoor seating options, while a small shed is visible to the right.

Chalet in Bessemer

Hot Tub • Fireplace • Dog Friendly •Big Powderhorn

My place is located at Big Powderhorn Ski Resort and close to Lake Superior, family-friendly activities, great views, restaurants and dining. You’ll love my place because of the location, the ambiance, the outdoor space, and the neighborhood. My place is good for couples, solo adventurers, and families (with kids). Dog friendly! Outdoor Hot Tub! Wood burning Fireplace with wood supplied! Great cell service! TV, Cable, Roku, WIFI....great entertainment! Washer/Dryer

The exterior of a charming white house is adorned with a thick blanket of snow. Icicles hang from the eaves, and large windows frame the entrance, showcasing symmetrical shutters on either side. A snow-covered path leads to the front door, inviting guests inside.

4.93 out of 5 average rating, 260 reviews

The Cookie Cottage

Beautiful home built in 1930. Now newly remodeled with 4 bedrooms and 2 full bathrooms. Located 7 easy blocks from downtown Ironwood. One king bed, and 3 queen beds. Quiet neighborhood. Great launching point for any local activity. Nordic ski trails less then 4 miles away; downhill skiing, snowshoeing, road and mountain biking, kayaking and hiking are all very close by. Self check in but always available for help. Sorry no pets, and no events/parties allowed.

4.98 out of 5 average rating, 173 reviews

The exterior of Yooper Delights Baking Co. features a welcoming yellow door and large window. Colorful signage displays various offerings, while flowering plants adorn the entrance. A white table and chairs provide a cozy outdoor seating area, enhancing the inviting charm of the bakery.

Cottage in Ironwood

Bakery Bunkhouse - Sweet Amenities & Nature !

Yooper Delights Baking Co. is now a family style home with beds for 7 ppl, a large, fully stocked kitchen, Scandinavian cottage design with 2 sleeping lofts plus a queen sleeper on main level, oak dining table for 8, Swedish gas fireplace, patio doors to back yard with firepit, gas grill & relaxing patio for outdoor dining & watching our visiting deer! We are located 2 miles from town, on outskirts, semi rural & peaceful , close to trails & Lake Superior!

A charming red farmhouse is set against a snowy landscape, surrounded by trees. The sky is bright with scattered clouds, enhancing the wintry scene. A small outbuilding is visible nearby, while a vintage bicycle is seen resting in the foreground.

4.98 out of 5 average rating, 234 reviews

Our Finnish Farmhouse: Book early for ski season

Note: No Smoking, vaping, or cannabis anywhere on property and no pets allowed. Our Finnish Farmhouse is a log home that was first established in 1906. The home was purchased and completely renovated and restored from 2016-2020. The original logs have been restored on the interior of the home and many updates have been made. We are sure you will enjoy your stay with us.

Popular amenities for Ironwood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.88 out of 5 average rating, 88 reviews

The exterior of the A-frame chalet is showcased, featuring a sloped red roof and striking black and red paneling. A spacious wooden deck surrounded by snow includes several benches, while leafless trees provide a serene backdrop.

Cabin in Bessemer

The Campfire Lodge @ Big Powderhorn with Hot Tub

4.96 out of 5 average rating, 80 reviews

A log cabin is positioned against a vibrant sunset sky, with the warm glow of a campfire in the foreground. The porch features seating arrangements, and the surrounding grassy yard is accented with potted plants. The scene evokes a sense of tranquility.

Chalet in Ironwood

Stunning Log Cabin Getaway at The Hannu Haus

4.98 out of 5 average rating, 102 reviews

A spacious living room features a cozy sofa, a decorative table, and a work desk. Skylights provide abundant natural light, enhancing the soft color palette. Elegant art pieces and antique mirrors add character to the room, complemented by warm lighting fixtures and a welcoming atmosphere.

Loft in Ironwood

* New, Luxury* The Powerhouse Loft

4.96 out of 5 average rating, 123 reviews

A three-story cabin is nestled within a snowy landscape, surrounded by tall trees. Its peaked roof and large balconies offer charming outdoor spaces. A gentle slope is noted in the foreground, blanketed in fresh snow, with the cabin appearing inviting and secluded.

Chalet in Bessemer

Big Chalet with Hot Tub on Big Powderhorn Mountain

4.87 out of 5 average rating, 163 reviews

The exterior of the chalet features a two-story structure with green siding and white trim. A wooden deck with railings is accessible by stairs, surrounded by tall trees that provide a natural setting. Large windows invite natural light into the interior.

Chalet in Wakefield

Indianhead duplex chalet with a hot tub 2376

5 out of 5 average rating, 29 reviews

Cabin in Ironwood

*HOT TUB* 6 Mile Hideaway

4.94 out of 5 average rating, 17 reviews

A two-story cabin features a wooden exterior with warm orange hues. Multiple balconies are visible, framed by sturdy railings. Snow covers the ground and roof, while a brick chimney adds character to the structure. Dark windows contrast with the bright surroundings.

Apartment in Bessemer

Lumberjack #3 Trailside Skiing Black River Basin

A spacious property is depicted, featuring a large lawn with well-maintained grass. Multiple buildings are visible, including a two-story house and adjacent structures, all set against a clear blue sky and surrounded by trees.

4.93 out of 5 average rating, 27 reviews

Cheerful 4-bedroom home with a hot tub

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 146 reviews

A Scandinavian-style cabin is elevated among autumn trees, showcasing a welcoming, rustic exterior. Two Adirondack chairs are positioned around a fire pit, which is surrounded by a circle of smooth rocks. The forest setting adds a serene backdrop to this outdoor gathering space.

Cabin in Bayfield

Romantic Vineyard Cabin, Sauna, Plunge Pool

4.85 out of 5 average rating, 250 reviews

An elevated deck features four outdoor chairs arranged for relaxation, overlooking a peaceful wooded area. Large glass doors reflect the surrounding greenery, allowing natural light into the interior space. The wooden deck surface provides a rustic charm with a welcome mat at the entrance.

Flat in Arbor Vitae

Retreat B on Little Spider Lake (Towering Pines)

4.95 out of 5 average rating, 55 reviews

A rustic log cabin is nestled among tall trees, bathed in warm sunlight. Four wooden adirondack chairs are arranged around a circular fire pit, surrounded by stones. Sunlight streams through the tree branches, casting gentle shadows on the grassy ground.

Cabin in Conover

Sasquatch Sanctuary Log Cabin | Sauna | 10 Acres

4.92 out of 5 average rating, 241 reviews

The exterior of a single-story home is presented, showcasing a light blue façade, a red front door, and an attached garage. A driveway leads to the garage, with a well-maintained lawn and trees visible in the surrounding area.

Home in White Pine

Comfy and Cozy by the Porkies

A charming house is set against a backdrop of green lawn and towering trees. The property features a sloped yard, with the entrance visible from the side, framed by vibrant foliage. A clear sky enhances the peaceful ambiance of the outdoor space.

4.87 out of 5 average rating, 47 reviews

Hiawatha’s Hideaway-cozy 2BR getaway, near trails

4.86 out of 5 average rating, 166 reviews

A grassy area is visible, leading up to several wooded cabins. A pathway ascends gently, flanked by trees. In the foreground, outdoor furniture is covered, with a circular gazebo and a shared space for activities situated nearby.

Cabin in Marenisco

Great cabin with a view, On Lake Gogebic.

The dining room features a round wooden table surrounded by four wooden chairs. A decorative chandelier hangs overhead. A sideboard positioned against the wall showcases a round mirror and a small lamp. Bright natural light enters through a doorway leading to another room.

5 out of 5 average rating, 9 reviews

Cozy and Colorful Bungalow

4.88 out of 5 average rating, 78 reviews

Two rustic wooden adirondack chairs are positioned on sandy soil, facing a serene sunset over Lake Superior. The sky displays hues of orange and pink as sunlight reflects on the water's surface, creating a peaceful atmosphere.

Cabin in Wakefield

Superior Sunset Cabin

Family-friendly home rentals with a pool

5 out of 5 average rating, 4 reviews

A comfortable living area is highlighted by a dark leather sofa adorned with red and white decorative pillows. A stone fireplace is featured in the corner, with a wooden wall art piece showcasing geometric patterns above. A framed vintage ski poster adds a charming touch to the decor.

Chalet in Upson

Ski Chalet of Whitecap Mountain

A cabin is surrounded by tall trees and features a spacious screened porch. Four Adirondack chairs and a fire pit are situated on the grass in front of the cabin. A barbecue grill is available nearby, with firewood stacked nearby for convenience.

Cabin in Sayner

Innisfree Cabin on Plum Lake

The living area showcases a cozy seating arrangement with a large gray couch and a wooden bar-height table. A stone fireplace serves as a focal point, with a flat-screen television mounted above. Natural light enters through glass doors, leading to an outdoor balcony.

Cabin in Upson

4.75 out of 5 average rating, 4 reviews

4BR/3BA Chalet-WiFi-AC, ATV, Hike, Ski-InOut, Hunt

A modern kitchen area features a circular marble-topped table surrounded by four upholstered stools on chrome bases. Natural light enters through large windows, illuminating the wooden cabinets and gray flooring. Kitchen appliances are visible, providing a functional yet stylish atmosphere.

Apartment in La Pointe

5 out of 5 average rating, 3 reviews

The Madeline Escape

A living area is framed by a stone wall with a fireplace and natural light filtering through window treatments. Comfortable seating is arranged around a wooden coffee table, with throw pillows adding texture. A staircase leads to the upper level, enhancing the home's open design.

Apartment in Upson

4.9 out of 5 average rating, 20 reviews

Whitecap Mountain: Mountain Meadows #4 Nitecap

A handcrafted cabin features rustic wood construction and large windows. Surrounded by lush greenery, the structure is set on a manicured lawn. The porch showcases logs supporting the roof, along with a stone patio area. Sunlight filters through the trees, highlighting the natural setting.

Cabin in La Pointe

4.61 out of 5 average rating, 99 reviews

Magical Handcrafted Cabinilicious in Magazines

4.75 out of 5 average rating, 24 reviews

A well-appointed bedroom features a spacious bed with crisp white linens, framed artwork on the wall, and bedside lamps providing soft illumination. A closet with double doors and a plush bathrobe are visible, contributing to the room's comfort and convenience.

Flat in Bayfield

Brookside Hide-A-Way #2, Port Superior, Bayfield