Family-friendly vacation 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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Guest favorite

Home in Ashland

4.87 out of 5 average rating, 229 reviews

Entire- Cozy Chequamegon Home

Escape suburbia at our quaint farm style house about a mile from Lake Superior and about 1/2 mile from Northland College. Guests describe our home as cozy & reminiscent of visiting their favorite coffee shop. The house offers 4 bedrooms, 1 full bathroom on the second floor & a half bath on the main floor. A portable crib is available for infants (30 1b max). Please note that we are in the process of having baseboards milled by a local crafts person who is also installing them when we are closed.

Guest favorite

Yurt in Bayfield

4.94 out of 5 average rating, 429 reviews

Twisting Twig Gardens and Orchard Rustic Yurt

Our yurt offers a sweet retreat in the woods about 10 miles outside of Bayfield. We are located on a small working organic farm with vegetable gardens, apple trees, and rustic accommodations. We are close to great outdoor recreation near Lake Superior and are about 6 miles from Meyers Beach in the Apostle Islands National Lakeshore. Our property is located on 40 acres and is very remote. We are on the edge of thousands of acres of county land. The perfect escape!

Guest favorite

Bungalow in Ironwood

4.86 out of 5 average rating, 227 reviews

Quaint and Colorful Bungalow

My place is close to the main East-West Highway, but in a quiet neighborhood. It is near cross country ski trails, snowmobile trails, hiking trails, yet there are restaurants and dining within walking distance. You’ll love my place because of the neighborhood and the colorful coziness. It is easy to access from the road, or from the backyard. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Guest favorite

Chalet in Bessemer

4.94 out of 5 average rating, 232 reviews

Hot Tub! Fireplace! The Wüdenknipple - 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). Outdoor Hot Tub! Wood burning Fireplace with wood supplied! Great cell service! TV, Cable, Roku, WIFI....great entertainment! Washer/Dryer

Superhost

Yurt in Bayfield

4.95 out of 5 average rating, 325 reviews

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 (mountain bike, cross-country ski and hiking). Enjoy panoramic views of Lake Superior including; Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton and Michigan) and the Upper Peninsula of Michigan. Come prepared to relax, unwind and explore the wonders of the north woods.

Guest favorite

Chalet in Wakefield Township

4.91 out of 5 average rating, 108 reviews

Ski Haus Chalet-Upstairs

Fall Colors are here!! We are a 10 minute walk/1 minute drive to Jackson Creek. Come and get the U.P experience! We are offering our upstairs second floor private chalet for rent. It is located close to Jackson Creek Ski Resort within Jackson Creek Village. A perfect rental for a large family, a couple families or larger group of friends. Our Chalet is within 15-30 minutes of awesome hiking, waterfalls and great outdoor activities.

Guest favorite

Home in Hurley

4.98 out of 5 average rating, 98 reviews

The FarmHouse

Turn of the century 4 bedroom 2 bath charming farmhouse, that has been lovingly restored. Set in Kimball WI, this farmhouse sits on 80 acres of rolling pastures and old growth hardwoods. Experience the peace and serenity when you stay in this spacious, renovated four-square farmhouse located three miles west of Hurley. Enjoy watching the wildlife activity in the apple orchard as you sip your morning coffee on the beautiful front porch.

Guest favorite

Cabin in Washburn

4.95 out of 5 average rating, 197 reviews

The Long House

My place is close to Lake Superior and the Apostle Islands It is located 2 miles north of Washburn or 10 miles south of Bayfield. Peaceful country setting, the long house is a freshly remodeled mobile home. Sorry, no pets. I have increased the number of guests to six . There are 4 double beds in the cabin. If you are booking with more than 4 guests, please allow for this. Thanks you! Open June 1 - mid October

Guest favorite

Cabin in La Pointe

4.86 out of 5 average rating, 232 reviews

7 Pines La Pointe on Madeline Island

NEED ISLAND SERENITY? Instant Book 7 Pines La Pointe on Madeline Island today! Come see how this 2 bedroom/2 bath cabin offers tranquility and peace in one of the more far away desired destinations in all of the country. Beautiful high peaked windows and glass doors, with a very large deck located in a forest of trees on the picturesque/historic Madeline Island, allow guests the feeling of going back in time.

Guest favorite

Home in Wakefield

4.99 out of 5 average rating, 95 reviews

Sasquatch Lodge Vacation Home

WE NOW HAVE A/C! Located on Indianhead Mountain in the western UP of Michigan, close to great views and family-friendly activities. Sasquatch Lodge is great for multiple couples, families, and big groups. Purposely designed to maximize 3500 square feet of space, providing plenty of room and privacy for our guests. Sasquatch is located just a few blocks from Indianhead (SnowRiver)

Superhost

Home in Ironwood

4.85 out of 5 average rating, 110 reviews

Granite Upper

Tucked up on the hills of Ironwood, Granite Getaway's 1400 sq. ft. upper unit has a peaceful setting that is close to snowmobiling, skiing, snowshoeing, waterfalls, fishing, Lake Superior lakeshore, hiking trails as well as several popular ski resorts. You are just minutes from downtown Ironwood, MI and Hurley, WI.

Guest favorite

Chalet in Bayfield

4.97 out of 5 average rating, 115 reviews

Northwoods Chalet @ Brickyard Creek

Tucked away in the Northwoods is your new favorite vacation locale. This recently built Brickyard Creek property is a single-level home featuring in-floor heat, a gas fireplace, three-season porch, and vaulted ceilings. The modern interior has been thoughtfully curated with minimalism and functionality in mind.