Holiday houses 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.

Family · Value · Backyard

The MacArthur House

Four generations of our family have resided at The MacArthur House. Formally a farm house it is a quaint & charming home with many of its original features. The kitchen has a chalkboard that came from one of the local schools. The house is located in a quiet residential neighborhood in close proximity to the local schools,colleges & hospital. We are licensed. We love animals, but we do not invite pets to stay on our property. We also do not allow smoking, or tobacco anywhere on our property.

Location · Family · Checkout

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!

Value · Family · Comfort

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.

Family · Value · Biking

Lakeview Condo: Downtown Bayfield, Beach, Deck

Experience the charm of Bayfield in our spacious top-floor condo with breathtaking views of Lake Superior.  Perfectly situated, it's an ideal spot for sunrise enthusiasts & offers quick access to downtown. Enjoy the comfort of modern living in a serene lakeside setting. Walk to shops, restaurants, & the island ferry, or relax on the deck overlooking the lake. • 3 bedrooms + loft, sleeps 8 • 2.5 bath, fully stocked kitchen • Deck w/ dining table • Smart TV w/ streaming • Washer/dryer

Family · Value · Laundry

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.

Family · Location · Solo travel

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.

Location · Value · Hiking

"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 !!!

Family · Value · River

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.

Value · Location · Long stay

Hilltop Acres - Hike-Bike-Ski-Sled-ATV-Hunt-Fish

Hilltop Acres located in Historic Montreal, WI, just 3 miles from Hurley, WI, is in a quiet location on Trimble Hill. The backyard is adjacent to acres of woods containing the Historic Montreal Ski Trails in winter. For snowmobile & ATV enthusiasts, trails are accessible from the house. Plenty of parking for trailers. Hunting, fishing, alpine skiing & golf nearby as well as the Gile Flowage, many water falls, rivers & lakes to explore!

Location · Family · Nearby

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.

Value · Family · View

The Garland City Downtown Apartment

1920s, craftsman and art-deco-inspired apartment, furnished with antiques, located in the heart of Ashland’s Main Street Historic District. Ditch the car and walk to local amenities like the grocery store, brewpub, bars, restaurants, shops, library, and movie theater. View Ashland’s downtown murals. The Lake Superior waterfront is steps away...where you can stroll the shoreline path or bicycle the 9-mile town loop.

Location · Value · Cleanliness