Family-friendly vacation rentals in Ashland County

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!

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!

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 & Mt Ashwabay nordic ski/ hiking trails). Enjoy panoramic views of Lake Superior including, Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton & Michigan) & the Upper Peninsula of Michigan. Come prepared to relax, unwind & explore the wonders of the north woods. Yurt access walk in only & is 3/4 mile uphill.

The Shell Cabin at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Shell Cabin, with opportunities for skiing, snowshoeing, hiking, and all the outdoor adventures. Take in the views from your back deck, relax around the bonfire, enjoy walk to Lake Superior, hike or snowshoes the North Country Trail to waterfalls or take a day trip to the Porkies. Don't forget to visit Downtown Ironwood and experience its charm for yourself. Amazing star gazing and Northern Lights potential! 420 Friendly for 21&up.

Cozy Home onTrail|Sauna|PetsI Lakes Trails Falls

Welcome to Little House on The Trail!—perfectly located near the Porcupine Mountains, Lake Superior, waterfalls and hiking trails. This spotless, thoughtfully designed home blends vintage charm with modern comfort, featuring a fully stocked kitchen & coffee bar. Unwind in the cedar sauna or gather around the firepit. Pets ok, spacious, and packed with amenities, it’s the perfect Northwoods getaway year-round. ⭐ Guests consistently say this is the best Airbnb they’ve stayed in—come see why!

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.

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.

Renovated 19th Century UP Getaway in Ironwood

Enjoy a this late 19th century in this centrally-located and renovated home in Ironwood. 3 Bedroom/ 1.5 bath house in Ironwood, MI within walking distance of restaurants. Access to snow mobile trails across the street. Close to parks and trails. Cook your own meals in or dine locally. Park your trailer with your ATVs in the driveway or keep your equipment in the 2-car garage. Use the house as a launching pad for your UP adventures while you explore the entire UP or Northern WI.

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 A

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.

Superior Sunset Cabin

An off-grid cabin on a bluff overlooking Lake Superior, with staircase to your own beach access. Sunsets every night (weather permitting...) Technological detox in a pristine area, just a 25 minute walk from the Presque Isle Scenic Area, the most beautiful part of the Porcupine Mountains. NOTE: This is an OFF-GRID cabin, with limited amenities to help you reconnect with Nature and the present moment. Read on for full details. *** If bringing pets, please pay the pet fee ***

Bungalow (House) on Chequamegon Bay.

This newly renovated fully furnished home is located within one block from beautiful Chequamegon Bay, Ashland's Oredock Pier, walking and bike trail, boat ramp, and beach. Grab a pole and head down to fish off the Ashland Oredock pier, or pack up for picnic at the beach, launch your boat, kayak or canoe. Take a walk, bike, or run on the walking trails. It is short walk to a few local restaurants and the downtown area. Access snowmobile trails. No pets are allowed.