Family-friendly holiday rentals in Ashland

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Top-rated family-friendly rentals in Ashland

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

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Guest favourite

Home

4.87 out of 5 average rating, 230 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 favourite

Home

4.9 out of 5 average rating, 197 reviews

Kinney Valley Farm

This rustic, but modernized farmhouse is on 110 acres of woods and apple orchards. Snow is great now! Cross country ski trails are " skier-groomed" on our property. Multiple areas for groomed skiing are within 30-45 minute drives. Located just 3 miles from the south shore of Lake Superior, and 30 minutes from the Apostle Island Sea Caves, spectacular now with winter ice sculptures, Kinney Valley Farm is a cozy place to stay, while exploring the pastoral winter beauty of Northern Wisconsin.

Guest favourite

Cabin

4.93 out of 5 average rating, 139 reviews

Log Cabin at Spider Lake

Step back in time in an authentic seventy year old hand hewn log cabin located on a northern Wisconsin lake with no public access. The cabin has all modern amenities. Rental includes two kayaks, a canoe, a 14 foot fishing boat, and two bicycles. The cabin sits of 1.5 wooded acres with 300 ft. of lake frontage. There is no WIFI in the cabin. WIFI is available 3 miles away at the Iron River library 24/7. The cabin has cell service. Nightly rate includes state and local occupancy tax

Guest favourite

Cottage

4.98 out of 5 average rating, 254 reviews

The Cottage WE HAVE SNOW! Access to Trails!

We are an event center but do not have events or weddings during your stay. This cozy one-bedroom cottage is set against the tree line. In the morning, enjoy coffee on the private porch, go snowshoeing, hiking, fishing, or canoeing in and around Brule River State Forest in the afternoon, and watch a few movies in the evening. Are you traveling with a group? Check out our other listing, The Farmhouse at Brule River Barn, a four-bedroom, two-bath home that can accommodate 11 guests.

Guest favourite

Yurt

4.94 out of 5 average rating, 431 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 favourite

Tiny home

4.97 out of 5 average rating, 396 reviews

Berrywood Acres Cabin

Berrywood Acres is located on the eastern shores of Lake Nebagamon. We are known for beautiful sunsets with quiet surroundings and located minutes from the famous Brule River, great hiking trails nearby and a 35 minute drive from Duluth/Superior or a bit further east to the Bayfield/Ashland area. The cabin is simple with all you need for a little RnR. Come relax on the porch and enjoy the view. We look forward to welcoming you to Berrywood Acres Cabin!

Guest favourite

Home

4.97 out of 5 average rating, 319 reviews

Classic Vintage Log Cabin on Lake Superior

Classic, Vintage Log Cabin on 2.5 acres right on Lake Superior - a cozy step back in time! 250 ft. of private bedrock shoreline. 3 Bedrooms: 2 Queen, 1 Dbl. Large updated 3/4 bath, kitchen, and indoor wood burning fireplace. Outdoor firepit, firewood and picnic table. WiFi, TV, and DVD. Close to restaurants, brewery, shops, parks, golf, lighthouse, museums, hiking, biking, skiing, snowmobiling. Send me an inquiry if you can only stay one night.

Superhost

Yurt

4.95 out of 5 average rating, 327 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 favourite

Cabin

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 favourite

Cottage

4.98 out of 5 average rating, 494 reviews

Cottage with Lake Superior & North Shore views

Tucked away on 1.5 acres in the middle of Duluth, this one-bedroom cottage has breath-taking panoramic views of Lake Superior, the Aerial Lift bridge and the St. Louis River. With the large property and surrounding trees, the home feels secluded but has wonderful access to hiking and biking trails, parks, beaches and all that downtown Duluth and Canal Park have to offer. License PL 17-099

Guest favourite

Home

4.94 out of 5 average rating, 259 reviews

Marengo River Cabin

Quiet, simple cabin with modern amenities overlooking the Marengo River on a dead end dirt road. Enjoy a peaceful getaway in the Northwoods. Many nearby hiking trails including Copper Falls State Park, St. Peter’s Dome, Swedish Settlement and more. Adjacent to 400 acres of public land with groomed cross country ski and snowshoe trails.

Guest favourite

Chalet

4.97 out of 5 average rating, 116 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.