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Family-friendly holiday rentals in Ashland County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Ashland County

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
Cottage in Ironwood

Bakery Bunkhouse - Sweet Amenities & Nature !

Yooper Delights Baking Co. is now a family style home with beds for 5. A large fully stocked kitchen (including bakery treats) Scandinavian cottage with a sleeping loft (queen+ single size bed) plus a queen sleeper sofa on main level, large antique dining table, Swedish gas fireplace welcome you ! The patio doors open to private patio, large back yard, picnic flower garden & wildlife viewing ! We are located 2 miles from town, in a semi rural, peaceful township, close to trails & Lake Superior!

KitchenFamilyBathroom

4.98 out of 5 average rating, 217 reviews
Guest favourite
Home in Hurley

Cedar Hill Retreat, King Bed, 108 Acres of Privacy

Winding up the driveway you are greeted by a home located on 108 acres of privacy, yet only 8 miles from town! This place is a clean (enhanced cleaning routine), fresh, and relaxing with breathtaking views! With enough space for a whole group or private couple getaway, this home offers the perfect opportunity to make memories lasting a lifetime. Gather around the wood stove after a long winter day full of activities available close by, or relax on the back deck watching the sun set in summer!

KitchenFamilyView

4.96 out of 5 average rating, 164 reviews
Guest favourite
A rustic red yurt is surrounded by a forest of trees. A large wooden deck offers a welcoming entrance and is equipped with a sturdy railing. Natural ground covers and underbrush can be seen nearby, creating a serene and natural setting.
Yurt in Bayfield

Bayfield Rustic Yurt 2 (Terra Cotta)

Nestled in the middle of the Bayfield County Forest, this rustic, minimally maintained yurt has direct access to miles of non-motorized rec trails (CAMBA single track & Mt Ashwabay nordic ski/ hiking trails). Enjoy panoramic views of Lake Superior including, Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton & Michigan) & the Upper Peninsula of Michigan. Come prepared to relax, unwind & explore the wonders of the north woods. Yurt access walk in only & is 3/4 mile uphill.

KitchenIndoor spacesAccess

4.95 out of 5 average rating, 414 reviews
Top guest favourite
The Shell Cabin exterior is surrounded by trees, featuring a light grey siding and a welcoming front porch with wooden steps. A white door with a decorative glass panel is flanked by windows, inviting entry into the cozy retreat.
Cabin in Ironwood

The Shell Cabin at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Shell Cabin, with opportunities for skiing, snowshoeing, hiking, and all the outdoor adventures. Take in the views from your back deck, relax around the bonfire, enjoy walk to Lake Superior, hike or snowshoes the North Country Trail to waterfalls or take a day trip to the Porkies. Don't forget to visit Downtown Ironwood and experience its charm for yourself. Amazing star gazing and Northern Lights potential! 420 Friendly for 21&up.

KitchenFamilyOutdoor spaces

4.96 out of 5 average rating, 607 reviews
Top guest favourite
Home in Ironwood

Cozy Home onTrail|Sauna|PetsI Lakes Trails Falls

Welcome to Little House on The Trail!—perfectly located near the Porcupine Mountains, Lake Superior, waterfalls and hiking trails. This spotless, thoughtfully designed home blends vintage charm with modern comfort, featuring a fully stocked kitchen & coffee bar. Unwind in the cedar sauna or gather around the firepit. Pets ok, spacious, and packed with amenities, it’s the perfect Northwoods getaway year-round. ⭐ Guests consistently say this is the best Airbnb they’ve stayed in—come see why!

KitchenIndoor spacesGetting around

4.99 out of 5 average rating, 229 reviews
Guest favourite
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!

Indoor spacesKitchenGrill

4.95 out of 5 average rating, 161 reviews
Top guest favourite
The cabin's exterior displays a modern A-frame design, surrounded by a lush forest. The patio area features blue adirondack chairs and a small table, inviting relaxation amidst nature. A circular window enhances the aesthetic, creating a connection between indoor and outdoor spaces.
Cabin in Bayfield

The Acorn of Little Sand Bay Dog Friendly

Modern-rustic, Aframe on 10 wooded acres; beautiful, simple décor, fully equipped kitchen, glass stove top, air-fryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, with a heated tile floor, walk-in shower. Towels, shampoo/conditioner/bodywash are provided. King bed in loft and NEW king gel memory foam bed on main floor. Smart TV, wi-fi. Woodstove heats the cabin perfectly as the main heat source. All wood is provided for woodstove and firepit. There is a minisplit heat/ac unit.

Indoor spacesFamilyWalkability

4.99 out of 5 average rating, 232 reviews
Top guest favourite
A charming red cottage is nestled among tall trees, showcasing a welcoming front with two white Adirondack chairs placed on a natural surface. Decorative flower arrangements hang near the entrance, surrounded by lush greenery and plants.
Guest house in Ashland

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

KitchenIndoor spacesHiking

4.99 out of 5 average rating, 423 reviews
Guest favourite
A renovated kitchen and dining area showcases wooden cabinetry and a spacious island. A dining table with multiple chairs is set up beside a wall adorned with artwork. Soft lighting enhances the welcoming atmosphere, while large windows bring in natural light.
Home in Ironwood

Renovated 19th Century UP Getaway in Ironwood

Enjoy a this late 19th century in this centrally-located and renovated home in Ironwood. 3 Bedroom/ 1.5 bath house in Ironwood, MI within walking distance of restaurants. Access to snow mobile trails across the street. Close to parks and trails. Cook your own meals in or dine locally. Park your trailer with your ATVs in the driveway or keep your equipment in the 2-car garage. Use the house as a launching pad for your UP adventures while you explore the entire UP or Northern WI.

Indoor spacesKitchenHospitality

4.87 out of 5 average rating, 130 reviews
Top guest favourite
Cottage in Bayfield

Superior Sanctuary: Refined Rustic in the Woods

Escape to the tranquil shores of Lake Superior in our charming retreat! Nestled within the serene Brickyard Creek Community, this modern haven offers a perfect blend of rustic elegance and contemporary comforts.  Immerse yourself in nature's beauty, unwind on the spacious screened porch, and cozy up by the fireplace. Your peaceful escape awaits. • Screened Porch with Swing Chairs • Access to Beach and Hiking Trails • Smart TV & Streaming • Modern Kitchen  • Boat Slip Rental A

KitchenIndoor spacesBack garden

4.88 out of 5 average rating, 205 reviews
Superhost
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! Strong Wifi updated in May 2026. This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. 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. The pool an restraunt opens July 1st. 5 minutes to Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

FamilyIndoor spacesAccuracy

4.79 out of 5 average rating, 396 reviews
Guest favourite
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

An off-grid cabin on a bluff overlooking Lake Superior, with staircase to your own beach access. Sunsets every night (weather permitting...) Technological detox in a pristine area, just a 25 minute walk from the Presque Isle Scenic Area, the most beautiful part of the Porcupine Mountains. NOTE: This is an OFF-GRID cabin, with limited amenities to help you reconnect with Nature and the present moment. Read on for full details. *** If bringing pets, please pay the pet fee ***

KitchenFamilyQuiet

4.91 out of 5 average rating, 100 reviews

Popular amenities for Ashland County family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
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.
Cabin in Ironwood

Handcrafted Log Cabin | Hot Tub | Sauna | GameRoom

Indoor spacesFamilyLaundry

4.96 out of 5 average rating, 114 reviews
Guest favourite
A dining table is set with a neutral table runner and a decorative centerpiece featuring flowers. Surrounding the table are four white chairs, with natural wood walls adding warmth to the space. Large windows with subtle curtains provide ample natural light, illuminating the cozy interior.
Chalet in Bessemer

Hot Tub • Sauna • Fireplace • Big Powderhorn

FamilyIndoor spacesLong stay

4.94 out of 5 average rating, 236 reviews
Top guest favourite
The exterior of the renovated chalet is shown, featuring red wood siding and multiple levels. A spacious deck is visible, equipped with seating and surrounded by greenery. Solar panels are installed on the roof, and a garden area is located below.
Chalet in Ironwood Township

Hot Tub | Sauna | King Bed | AC | Pets |Micro Farm

FamilyKitchenParks

4.97 out of 5 average rating, 136 reviews
Guest favourite
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

KitchenFamilySkiing

4.93 out of 5 average rating, 307 reviews
Guest favourite
Apartment in Wakefield

Cozy & Clean 2B/2B Condo w/ Jetted Tub!

KitchenFamilyComfort

4.97 out of 5 average rating, 215 reviews
Guest favourite
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

KitchenFamilyAccess

4.97 out of 5 average rating, 123 reviews
Guest favourite
Cabin in Bessemer

The Campfire Lodge @ Big Powderhorn with Hot Tub

Indoor spacesFamilyValue

4.89 out of 5 average rating, 103 reviews
Guest favourite
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

FamilyIndoor spacesHiking

4.87 out of 5 average rating, 170 reviews

Family- and pet-friendly home rentals

Top guest favourite
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

KitchenIndoor spacesView

4.97 out of 5 average rating, 319 reviews
Guest favourite
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.
Home in Ironwood

Park Place - Updated Home Close to Downtown

Indoor spacesKitchenDecor

4.95 out of 5 average rating, 195 reviews
Guest favourite
The exterior of the unit is framed by mature trees, featuring two private patios with seating. Steps lead from the grassy area to the wooden deck, which is designed for relaxation in a tranquil setting. Large windows reflect the surrounding greenery.
Flat in La Pointe

Treehouse 1 on Madeline Island

FamilyKitchenAmenities

4.9 out of 5 average rating, 157 reviews
Guest favourite
A cozy bedroom features a metal bed frame with a soft blanket. Two bedside tables with lamps are placed symmetrically on each side. Colorful artwork is displayed on the walls, adding character. Natural light brightens the space, enhancing the calming atmosphere.
Flat in Bayfield

Sunrise Lake View 2 • Walk to Downtown Bayfield

Indoor spacesFamilyAccess

4.93 out of 5 average rating, 167 reviews
Guest favourite
A single-story home with a light grey exterior is showcased, featuring a central entrance with a white door and two large windows. Snow-covered grounds and trees in the background enhance the scene. The driveway is partially visible, bordered by a front lawn.
Home in Ironwood

U. P. Delight 2 bedroom home

FamilyKitchenBiking

4.9 out of 5 average rating, 158 reviews
Guest favourite
A cozy cabin is nestled among tall trees, featuring a green metal roof and large windows. A well-kept yard of green grass surrounds the cabin, with a white chair on the porch and a log in the foreground, creating a serene outdoor space.
Cabin in Ironwood

Quinn-A-Witz Cozy Cabin

Indoor spacesKitchenBiking

4.74 out of 5 average rating, 141 reviews
Top guest favourite
Home in Bayfield

Walk to Shops & Lake/Hiking, EV Charger, Fire Pit!

Indoor spacesKitchenAccuracy

5.0 out of 5 average rating, 68 reviews
Top guest favourite
A serene lakefront view showcases a dock leading to Fisher Lake, where boats are seen anchored. The setting sun casts a warm glow over the water, while a tall tree stands beside the dock. Lounge chairs and a firepit area are visible in the foreground.
Cabin in Mercer

On ATV Trail & a 3-Lake Chain w/Water Trampoline!

FamilyIndoor spacesBeach

4.99 out of 5 average rating, 72 reviews

Family-friendly home rentals with a pool

Superhost
Apartment in Bayfield

Superior Hideaway

FamilyIndoor spacesAmenities

4.74 out of 5 average rating, 233 reviews
Guest favourite
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

The Madeline Escape

FamilyLocationView

5.0 out of 5 average rating, 7 reviews
Guest favourite
Apartment in Bayfield

Hidden Gem, 3 Bed Cozy Condo - Dogs Welcomed

Indoor spacesKitchenGrill

4.83 out of 5 average rating, 47 reviews
Superhost
Flat in Bayfield

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

FamilyIndoor spacesAir conditioning

4.79 out of 5 average rating, 28 reviews
Guest favourite
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

Indoor spacesKitchenOutdoor spaces

5.0 out of 5 average rating, 6 reviews
Superhost
Flat in Bayfield

Brookside Condo #4

Indoor spacesHospitalityCleanliness

4.86 out of 5 average rating, 14 reviews
Superhost
Flat in La Pointe

Madeline Island Beachfront Condo - up to 10 guests

New place to stay
Guest favourite
Home in Upson

Lakefront 5 Bedroom 3 bath Northwood Chateau 2 & 4

FamilyOutdoor spacesAmenities

5.0 out of 5 average rating, 5 reviews

Destinations to explore