Kid-friendly holiday rentals in Ashland County

Downtown "Green Room" at Villages on Aurora

Welcome to our downtown getaway! Village on Aurora is located in the heart of downtown Ironwood putting you steps away from Ironwoods City Square and the Historical Ironwood Theater. Lake Superior is only a short drive North of Downtown leaving you minutes away from waterfalls, and beaches. Our area has a multitude of different types of trails (hiking, biking, cross country, snowmobile, ATV) many just steps from your front door. Electric car chargers are also available in the downtown area makin

One Minute Walk to Lake Superior. Brookside #11

Amazing location! This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. Strong Wifi, balcony, AC, CableTV , BBQ, 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, ski and more!! The pool and restraunt opens July 1st. 5 minutes from Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

Cheerful, Charming Retreat

Enjoy a stylish experience at this centrally-located place; it’s a hidden treasure. Enjoy walking to restaurants, and adventure surrounding Hurley’s historic Silver Street while being able to retreat to a place of your own. Conveniently located close to the Iron Horse Trail. Waterfalls, skiing, kayaking, mountain biking are all adventures close by. Start your morning with a cup of coffee in the beautiful three-season porch, and end your day with your favorite drink under the glowing chandelier!

Superior Sanctuary: Refined Rustic in the Woods

Escape to the tranquil shores of Lake Superior in our charming retreat! Nestled within the serene Brickyard Creek Community, this modern haven offers a perfect blend of rustic elegance and contemporary comforts.  Immerse yourself in nature's beauty, unwind on the spacious screened porch, and cozy up by the fireplace. Your peaceful escape awaits. • Screened Porch with Swing Chairs • Access to Beach and Hiking Trails • Smart TV & Streaming • Modern Kitchen  • Boat Slip Rental Available

Mountain Top Chalet ~ A/C & Close to Rec Trails!

Located right off Big Powderhorn's Lift 1, Mountain Top Chalet has everything you're looking for in a vacation rental! Tucked into the woods and fully remodeled with your comfort in mind, this private, beautiful home has everything you could want and more! There are 3 levels to this home, 2 living spaces each with a wood burning fireplace, 4 comfy bedrooms and a large loft area dedicated to hosting kids. This home is perfect for large group getaways at any time of the year!

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

Indianhead Red Lodge by Ski Resort

We are offering our vacation home to rent. It is located right down the road from Indianhead Ski Resort. Our favorite place to be! 1500 sq ft of room to spread out. A perfect rental for a large family, a couple families, or adult time away without the kids. The property sits on 5 acres of wooded land scattered with seasonal wildflowers. The property has plenty of room to park snowmobile/ATV trailers. The trails are close by.

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.

Cozy remodeled cottage in heart of Ashland

Cozy little cottage in quiet neighborhood in Ashland. Only five blocks from Chequamegon Bay. Completely remodeled in 2019. Home features two cozy bedrooms with queen sized beds. All new furniture and appliances. Nice deck with backyard to enjoy your morning coffee or evening meals. Downstairs area with large sectional sofa for kids, teenagers and Dad to get away by themselves!