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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Guest favourite

Home in Ashland

4.87 out of 5 average rating, 235 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.

Superhost

Yurt in Bayfield

4.87 out of 5 average rating, 503 reviews

Bayfield Rustic Yurt 1 (Evergreen)

Explore thousands of acres of the Bayfield County Forest and enjoy endless miles of exceptionally maintained non-motorized recreational trails. The yurt has direct access to CAMBA mountain bike trails and Mt. Ashwabay ski trails. The landscape is also spectacular. Take in the panoramic views of Lake Superior and the Onion River valley. This is a rustic, minimally maintained yurt set in the middle of the county forest, so come prepared to relax, unwind and explore the wonders of the north woods.

Guest favourite

Chalet in Bessemer

4.96 out of 5 average rating, 113 reviews

Big Chalet with Hot Tub on Big Powderhorn Mountain

This is it! Our place is a great place for your big family or group to ski, snowmobile or just relax. We offer plenty of room with 5 private bedrooms. We have an area of open space including a living room and kitchen that is MASSIVE. It has 2 fireplaces. A gas fireplace in the living room and if you prefer wood there is a wood one in the kitchen. Time to clean up, we have 3 full bathrooms stocked with shampoo, conditioner, soap. Then a sauna and hot tub to relax. Also a rec room Wi Fi

Top Guest favourite

Home in Ironwood

4.99 out of 5 average rating, 214 reviews

Free Breakfast | Close to Waterfalls | Fast Wi-Fi

☀️ PRIME LOCATION ☀️ Close to waterfalls/hiking & dining. (View our listing Guidebooks for more details) Five blocks north of US2, set amid peaceful surroundings, our cozy, immaculate, well-appointed home, provides a blend of comfort & convenience, ensuring your stay feels like home. ❖ What our guests say ❖ “Sue provides extra touches we’ve never experienced at another stay." “This was the best Airbnb I’ve ever stayed in & I’ve traveled the world.” ❖ CONTACT US FOR EXTENDED STAY RATES ❖

Superhost

Tent in Bayfield

4.88 out of 5 average rating, 165 reviews

Twisting Twig Gardens and Orchard Wall Tent

Our wall tent offers a sweet retreat in the woods about 10 miles outside of Bayfield. We are located on a small working organic farm with vegetable and perennial gardens, apple trees, and rustic accommodations. We are located 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 has a distant, but beautiful view of Lake Superior. We are on the edge of thousands of acres of county land. The perfect escape!

Superhost

Condo in Bayfield

4.79 out of 5 average rating, 159 reviews

One Minute Walk to Lake Superior. Brookside #10

Amazing location! This Comfy Studio Condo sleeps 4, King bed & Queen sofa sleeper. kitchen, balcony, AC, CableTV, Strong WiFi, BBQ, fire pit, jet-tub/shower. Walk to the restaurant, bar, marina and pool. The pool opens in July. Brookside is 2.3 miles from Bayfield. Hike or bike the Brownstone trail along the lake. Ride the ferry to Madeline or cruise the Apostles. Sail, fish, kayak, golf, orchards, ski. Mt Ashwabay, Big top , Bayview beach plus many trails within minutes.

Guest favourite

Chalet in Bessemer

4.95 out of 5 average rating, 252 reviews

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

Guest favourite

Condo in La Pointe

4.85 out of 5 average rating, 118 reviews

Sheila's Downtown Condo

Walk to absolutely everything! Golf course, marina, ferry, galleries, restaurants, grocery, live music, bike, moped and kayak rentals, museum, beaches. The 1 bdrm condo is located 1.5 blocks from the ferry landing and is right above the Mission Hill coffee shop. The Big Lake is 1/2 block away and can be viewed from the spacious living room windows along with spectacular sunsets. Please note that the condo is not directly on the lake.

Guest favourite

Cabin in Washburn

4.95 out of 5 average rating, 199 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

Top Guest favourite

Chalet in Wakefield Township

4.91 out of 5 average rating, 114 reviews

Ski Haus Chalet-Upstairs

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 favourite

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.

Top Guest favourite

Home in Wakefield

4.99 out of 5 average rating, 104 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)