
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.

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!
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Cozy Game Room+PetsI Near Lakes Waterfalls Trails
Cozy, fully stocked Ironwood retreat near Lake Superior—perfect for families & pets. Minutes to waterfalls, hiking trails, beaches & downtown. Sleeps 8 comfortably w, fast WiFi, smart TV & fully equipped kitchen. Enjoy a game room with ping pong, Pac-Man & darts, w/ private deck w/ wooded views, playhouse, creek & deer and turkey in backyard! Clean, spacious, and thoughtfully equipped for the ultimate getaway. ⭐ Guests consistently say this is the best Airbnb they’ve stayed in—come see why!
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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!
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Bayfield Fruit Loop Retreat - Main Cottage
Welcome to the Bayfield Fruitloop Retreat, featuring a beautiful "Main Cottage" nestled in 7 acres of woods in Bayfield, Wisconsin. The property allows you to savor a peaceful & quiet northwoods experience but still minutes from several attractions & historic downtown Bayfield. The property is conveniently located just 5 minutes' drive or 2.5 miles from the center of downtown Bayfield. Located right on country Hwy J, a starting point for a self-guided tour around the city of Bayfield where a
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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!
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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.
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Off grid Shasta trailer at Rockhound Hideaway
An outdoor enthusiasts dream awaits at Rockhound Hideaway's Sodalite Shasta with opportunities for snowshoeing, skiing, hiking, and ending the day with a steamy sauna. 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.
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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 and Mt Ashwabay nordic ski and hiking trails). 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. Yurt access is 3/4 mile uphill.
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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.
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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.
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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 spacesCleanliness

Hot Tub • Fireplace • Dog Friendly•Big Powderhorn
Located in the Village area of Big Powderhorn Ski Resort, this cozy A-frame offers comfort and convenience. Features include a covered HOT TUB to soothe your muscles at the end of a day of hiking, skiing or sledding. Close to Copper Peak, Lake Superior, waterfalls, bike trails and more. Inside you will find a wood FIREPLACE, 2 loft bedrooms with 4 beds, 1 full bath, fully equipped kitchen, Smart TV and WIFI. No cleaning fee!!!
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Popular amenities for Ashland County family-friendly rentals
Family-friendly home rentals with a hot tub

The Campfire Lodge @ Big Powderhorn with Hot Tub
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Crossbow Chalet is in the heart of the Northwoods
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Trailside Retreat#3- ski, snowboard, snowmobile
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Big Chalet with Hot Tub on Big Powderhorn Mountain
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* New, Luxury* The Powerhouse Loft
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Indianhead duplex chalet with a hot tub 2376
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*HOT TUB* 6 Mile Hideaway
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Hot Tub • Fireplace • Dog Friendly •Big Powderhorn
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Family- and pet-friendly home rentals

Trail Riders Haven-Heated Garage-1 Block ATV Trail
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Cedar Cove Cabin 2
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Trailside Retreat w/ Sauna+Game Room+Dog Friendly
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Park Place - Updated Home Close to Downtown
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Superior Sunset Cabin
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Ideal Northwoods cabin on Long Lake
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On ATV Trail & a 3-Lake Chain w/Water Trampoline!
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Quinn-A-Witz Cozy Cabin
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Family-friendly home rentals with a pool

Lakefront 5 Bedroom 3 bath Northwood Chateau 2 & 4
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Ski Chalet of Whitecap Mountain
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Ski-In/Ski-Out Condo in Upson - Walk to Lake
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One Minute Walk to Lake Superior. Brookside #3
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4BR/3BA Chalet-WiFi-AC, ATV, Hike, Ski-InOut, Hunt
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The Madeline Escape
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Whitecap Mountain: Mountain Meadows #4 Nitecap
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Brookside Hide-A-Way #2, Port Superior, Bayfield
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Destinations to explore
- Rentals with beach access Ashland County
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- Rentals with a hot tub Ashland County
- Ski-in/ski-out rentals Ashland County
- Hotel rooms Ashland County
- Chalet rentals Ashland County
- Pet-friendly rentals Ashland County
- Rentals with a sauna Ashland County
- Bed and breakfasts Ashland County
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- Rentals with a kayak Ashland County
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- Rentals with lake access Ashland County
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- Family-friendly rentals Wisconsin
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