Family-friendly vacation rentals in Ashland

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Top-rated family-friendly rentals in Ashland

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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

Home in Port Wing

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 favorite

Cabin in Iron River

4.93 out of 5 average rating, 139 reviews

Log Cabin and 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

Superhost

Home in Beaver Bay

4.9 out of 5 average rating, 100 reviews

Northwoods Luxury on Private Black Sand Beach

Beautiful waterfront all-season home with 260ft private lake shore! One of a kind sandy beach on Lake Superior, 3 bedrooms with dramatic lake views and everything you need to make your trip memorable. If you've experienced Minnesota's North Shore, you know the secret beauty that awaits. From hiking, skiing and the famous Gitchi-Gami Bike Trail, the only challenge is deciding what do first...that is, if you can peel yourself away from the private beach and your cup of coffee.

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

Tiny home in Lake Nebagamon

4.97 out of 5 average rating, 394 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 favorite

Home in Two Harbors

4.97 out of 5 average rating, 317 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 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

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

Cottage in Duluth Heights

4.98 out of 5 average rating, 490 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 favorite

Home in Mason

4.94 out of 5 average rating, 258 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 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.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Ashland family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Rental unit in Wakefield

4.84 out of 5 average rating, 19 reviews

Clean & Comfortable Condo - Walk to Jackson Creek

Guest favorite

Chalet in Bessemer

4.96 out of 5 average rating, 103 reviews

Big Chalet with Hot Tub on Big Powderhorn Mountain

Guest favorite

Chalet in Wakefield

4.85 out of 5 average rating, 150 reviews

Indianhead duplex chalet with a hot tub 2376

Condo in Ironwood

4.87 out of 5 average rating, 31 reviews

The NorthWoods Retreat 2

Guest favorite

Chalet in Bessemer

4.94 out of 5 average rating, 232 reviews

Hot Tub! Fireplace! The Wüdenknipple - Powderhorn

Condo in Bessemer

5 out of 5 average rating, 13 reviews

Lumberjack #3 Trailside Skiing Black River Basin

Condo in Bessemer

4.5 out of 5 average rating, 10 reviews

Unit #1 Lumberjack- Trailside Black River Basin

Condo in Ironwood Township

4.73 out of 5 average rating, 11 reviews

Rustic Luxury in the North Woods I

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Family- and pet-friendly home rentals

Guest favorite

Rental unit in Hayward

4.87 out of 5 average rating, 280 reviews

Sunset Lake View Apt Callahan Lake

Superhost

Cottage in Knife River

4.84 out of 5 average rating, 105 reviews

Be Still, relax, rejuvenate at River Bend Cottage

Superhost

Home in Minocqua

4.87 out of 5 average rating, 122 reviews

Cozy Cottage on the Island, Walkable to everything

Guest favorite

Home in Ontonagon

4.97 out of 5 average rating, 239 reviews

The Lake House

Superhost

Cabin in Superior

4.86 out of 5 average rating, 330 reviews

“The Bunk House” on Lake Amnicon. Pet Friendly!

Guest favorite

Chalet in Fifield

4.87 out of 5 average rating, 135 reviews

Cabin on the River Bank Built 2011

Guest favorite

Cottage in Marenisco

4.93 out of 5 average rating, 169 reviews

Whitley House

Guest favorite

Home in Duluth

4.89 out of 5 average rating, 433 reviews

Nice 3 bedroom house with a view

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Family-friendly home rentals with a pool

Home in Beaver Bay

4.74 out of 5 average rating, 23 reviews

Windsong 608 on Lake Superior in Beaver Bay, MN

Home in Beaver Bay

4.55 out of 5 average rating, 20 reviews

Windsong 610 on Lake Superior in Beaver Bay, MN

Condo in Bayfield

4.79 out of 5 average rating, 338 reviews

One Minute Walk to Lake Superior. Brookside #11

Condo in Bayfield

4.81 out of 5 average rating, 277 reviews

One Minute Walk to Lake Superior. Brookside #3

Condo in Downtown Duluth

4.64 out of 5 average rating, 67 reviews

Captain`s Canal Park Suite in Duluth`s Canal Park

Guest favorite

Condo in Bayfield

4.81 out of 5 average rating, 146 reviews

One Minute Walk to Lake Superior. Brookside #10

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Quick stats about vacation rentals that are family-friendly in Ashland

Total rentals
10 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
1K reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Deep Water Grille, El Dorado, and AmericInn by Wyndham Ashland

Family-friendly vacation rentals in Ashland

Top-rated family-friendly rentals in Ashland

Vacation rentals for every style

Cabins

Hotels

Unique stays

Popular amenities for Ashland family-friendly rentals

Family-friendly home rentals with a hot tub

Rental unit in Wakefield

Chalet in Bessemer

Chalet in Wakefield

Condo in Ironwood

Chalet in Bessemer

Condo in Bessemer

Condo in Bessemer

Condo in Ironwood Township

Family- and pet-friendly home rentals

Rental unit in Hayward

Cottage in Knife River

Home in Minocqua

Home in Ontonagon

Cabin in Superior

Chalet in Fifield

Cottage in Marenisco

Home in Duluth

Family-friendly home rentals with a pool

Home in Beaver Bay

Home in Beaver Bay

Condo in Bayfield

Condo in Bayfield

Condo in Downtown Duluth

Condo in Bayfield

Quick stats about vacation rentals that are family-friendly in Ashland

Total rentals

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Total number of reviews

Wifi availability

Popular amenities

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