Family-friendly vacation rentals in Ashland

Cozy Trailside Nordic Forest Cottage

Welcome to the Trailside Gökotta Forest Cottage: a modern, minimalist and serene nature cabin on the Birkie Trail system. Gökotta means 'to get up early to listen to sounds of birds and the forest'. Located right on Birkie Ridge Trailhead with close access to vast CAMBA trails, this is a nature escape for outdoor enthusiasts who love to bike, ski, hike, and bird watch. Enjoy ski-in ski-out to groomed trails, bike-in bike-out right onto trails, then cozy up by the woodstove or fire-pit at night.

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.

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.

Off grid Shasta trailer at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Sodalite Shasta with opportunities for snowshoeing, skiing, hiking, and ending the day with a steamy sauna. This off grid, cozy 14' trailer is situated on a two acre lot with two other rentals and my full time residence on the edge of the Ottawa National Forest. A short walk to Black River Harbor, the North Country Trail & Lake Superior, this is a perfect getaway for those seeking a rustic yet comfortable stay with a campy feel.

Adorable Northwoods cabin

Come enjoy the North woods in our beautiful little cabin. This cabin is a located in a perfect spot only 2 miles outside of Iron River. Close to tourist areas such as Duluth, Bayfield, Ashland and more. This cabin is the perfect get away. The Brule river is only 8 miles away and can make for the perfect day trip in a kayak or canoe. This cabin comfortably fits 2-4 people! You can enjoy the outdoors at the fire pit or the 3 season porch that gives you the perfect indoor/outdoor feeling!

Sylvan Chalet, Modern, Lakefront, Close to Trails

Built as a winter or summer escape for a couple or small group, this beautiful four season cabin is a great way to experience the Northwoods of Wisconsin in a modern, well-appointed, aesthetically rich space designed with relaxation in mind. Cabin is brand new as of January 2024. Host is 14 year "superhost" This is a default "no pets" cabin, however certain sizes and breeds are allowed by permission only. We have a NEMA 15-40R outlet for level 2 EV charging. You bring chord and adapter

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.

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.

Main Street apt 2 blocks from Lake Superior!

STELLA South Shore Stay is a new, gorgeous, one bedroom apartment just two blocks from Lake Superior, located on Main Street in Ashland, WI. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, and much more. Walk to Lake Superior in minutes, get a coffee at the Black Cat or a pastry at the bakery, or enjoy the many restaurants and shops on Main Street. You can also enjoy the many local hikes or check out the Apostle Islands.

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.

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.