Vacation rentals in Ashland County

The Cookie Cottage

Beautiful home built in 1930. Now newly remodeled with 4 bedrooms and 2 full bathrooms. Located 7 easy blocks from downtown Ironwood. Unfortunately not very close to the snowmobile trails. One king bed, and 3 queen beds. Great launching point for any local activity. Nordic ski trails less than 3 miles away; downhill skiing, snowshoeing, road and mountain biking, kayaking and hiking are all very close by. Self check in, but always available for help. Sorry no pets, and no events/parties allowed.

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.

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!

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

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.

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.

"Bakery Bungalow" -Sweet Accommodations & Nature !

Our Bakery Bungalow (owned by a baker) is a peaceful retreat in a semi rural, prime location near snow trail system, 2 miles from historic downtown shops, hiking / biking trails, on the outskirt of town (Ironwood Township) minutes from Big Powderhorn Mountain & Copper Peak, walking distance to Gogebic College & Mount Zion, 17 miles from Lake Superior beaches, large private wooded yard with fire pit, private parking, 1 stall garage if needed in winter. P.S. Bakery Treats provided !!!

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.

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.

Henny Penny-Quiet and Close to Town

This home is located on beautiful Madeline Island, less than a mile from the ferry dock and all La Pointe has to offer—beaches, shops, restaurants/bars, galleries, kayak rentals, marina, golf course and more! Easily bike or walk to town. Enjoy quiet evenings on the deck and added privacy, as the home is not visible from the road. Less than 1 mile from the Madeline Island Marathon start line and the Fourth of July parade and fireworks! 🎆

Romantic Vineyard Cabin, Sauna, Plunge Pool

Come and celebrate all that Bayfield has to offer at this quiet vineyard and forest getaway, just 2 miles from downtown. Located in Bayfield's charming Fruit Loop, you'll be surrounded by vines, forest, orchards, and berry farms. The Scandinavian cabin, forest facing sauna with plunge pool, and vineyard sit within acres of secluded woods. The cabin has an occupancy limit of 2 adults and one dog. There is a $40 pet fee.