
Family-friendly vacation rentals in Ashland County
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Top-rated family-friendly rentals in Ashland County
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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.

Camp on Main Street
2017 28ft Jayco Camper. Located downtown La Pointe; walking distance to shops, cafes, restaurants, bars, ferry boat, museum, golf course, marina, boat rentals, swimming pool, playgrounds. 2 min walk to Joni's beach. Tucked in our beautiful back yard (private to renter, not used by owner) behind the house we live. So close to everything but yet in the quietest part of Main Street. Ideal for families or couples. Max occupancy 4-6. Every person above 4 (approved only by host) is $30.00 a night.

The Copper Squirrel of Little Sand Bay DogsWelcome
A mature forest and a beautiful pond are what you'll see when you arrive at this cozy, secluded, full log cabin. The cabin was recently completely renovated (Mar/April 2025)from log to log and is stocked with everything you'll need for your stay. It has all new appliances, furniture, fixtures, bathroom, cabinetry. 💚 It is the perfect homebase to relax after a long day of hiking Frog Bay, Houghton Falls, Lost Creek Falls, Meyers Beach, or shopping in nearby Bayfield, Washburn, or Cornucopia.

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!

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!

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.

Off grid glamping at a Rockhound Hideaway
A perfect glamping retreat awaits you at Rockhound Hideaway's Agate Grove Bell Tent. Situated on a private two acre lot with two other rentals and my private residence in the Ottawa National Forest, steps from the Black River, North Country Trail and a one mile walk to the Lake Superior Shore, this is an ideal getaway for those seeking the adventure of camping with the comforts of home. Fall asleep to the sound nature and wake up to deer passing by as you enjoy your morning coffee.

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.

"Bakery Bungalow" -Sweet Accommodations & Nature !
Completely remodeled from head to toe! Located within half mile of trail system, 2 miles from historic downtown shops, on the outskirt of town (Ironwood Township=great drinking water) minutes from Big Powderhorn Mountain & Copper Peak, walking distance to Gogebic College & Mount Zion, 17 miles from Lake Superior, large private wooded yard with fire pit in summer, private parking, 1 stall garage if needed in winter. A light Bakery breakfast included with your stay!

Turtle Yurts - Yurt 1
1 Bedroom, 1 Bath, Sleeps 2 Nestled among the north woods, this yurt is a comfortable and unique getaway. The design is a contemporary twist on the traditional yurt, featuring classic yurt elements such as lattice walls and radial rafters, along with modern comforts. The yurt sleeps up to two guests with a queen-size bed sitting under a clear dome to watch the sky above. There is a sitting area, as well as a bathroom, complete with hot shower and flush toilet.

The Saari House on the ABR Ski Trails
The Saari House is a fully updated farmhouse located on the ABR ski trails. Ski on the freshly groomed trails right out the front door. (Trail passes required.) It's a perfect location for families skiing in and out on a winter getaway or as home base for local waterfall hiking or biking. Guests will have full kitchen, bathroom with tub/shower, washer/dryer, TV with collection of DVDs, various video games and board games.

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
Popular amenities for Ashland County family-friendly rentals
Family-friendly home rentals with a hot tub

Trailside Retreat#3- ski, snowboard, snowmobile

Big Chalet with Hot Tub on Big Powderhorn Mountain

* New, Luxury* The Powerhouse Loft

Indianhead duplex chalet with a hot tub 2376

*HOT TUB* 6 Mile Hideaway

Hot Tub • Fireplace • Dog Friendly •Big Powderhorn

Creekside Chalet | Largest Hot Tub in Western UP

Cute & Cozy 1B/1B Condo w/ Jetted Tub!
Family- and pet-friendly home rentals

Cottage Nestled in the Woods - Stolen Oaks

The Red Onion House near Bayfield

Trail Riders Haven-Heated Garage-1 Block ATV Trail

The Snuggery @ Whitecap ~ Ensuite Sauna

Trailside Retreat w/ Sauna+Game Room+Dog Friendly

Sunrise Lake View 2 • Walk to Downtown Bayfield

Superior Sunset Cabin

Rocky Pines U.P ~ Ski Area, Sauna, & Pets Allowed
Family-friendly home rentals with a pool

Lakefront 5 Bedroom 3 bath Northwood Chateau 2 & 4

Ski Chalet of Whitecap Mountain

Ski-In/Ski-Out Condo in Upson - Walk to Lake

One Minute Walk to Lake Superior. Brookside #3

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

The Madeline Escape

Whitecap Mountain: Mountain Meadows #4 Nitecap

Brookside Hide-A-Way #2, Port Superior, Bayfield
Destinations to explore
- Rentals with outdoor seating Ashland County
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- Bed and breakfasts Ashland County
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- Hotel rooms Ashland County
- Rentals with beach access Ashland County
- Rentals with an EV charger Ashland County
- Rentals with a sauna Ashland County
- Pet-friendly rentals Ashland County
- Rentals with a fire pit Ashland County
- Rentals with a hot tub Ashland County
- Ski-in/ski-out rentals Ashland County
- Rentals with a fireplace Ashland County
- Rentals with breakfast Ashland County
- Family-friendly rentals Wisconsin
- Family-friendly rentals United States
- Porcupine Mountains Wilderness State Park
- Whitecap Mountains Resort
- Big Powderhorn Mountain Resort
- Blackjack Mountain - Big Snow Resort
- Lutsen Mountains
- Apostle Islands National Lakeshore
- Copper Falls State Park
- Split Rock Lighthouse
- Porcupine Mountain Ski Resort
- Tettegouche State Park
- Gooseberry Falls State Park





