Family-friendly vacation rentals in Ashland

Entire- Cozy Chequamegon Home

Escape suburbia at our quaint farm style house about a mile from Lake Superior and about 1/2 mile from Northland College. Guests describe our home as cozy & reminiscent of visiting their favorite coffee shop. The house offers 4 bedrooms, 1 full bathroom on the second floor & a half bath on the main floor. A portable crib is available for infants (30 1b max). Please note that we are in the process of having baseboards milled by a local crafts person who is also installing them when we are closed.

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.

1 bedroom apartment with Lake Superior views!

STELLA South Shore Stay is a gorgeous, one bedroom apartment just two blocks from Lake Superior with beautiful lake views. Located on Main Street in Ashland. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, Duluth Coffee Co. coffee, 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. Also enjoy the many local hikes or the Apostle Islands.

Camp on Main Street

2017 28ft Jayco Camper. Located downtown La Pointe; walking distance to shops, cafes, restaurants, bars, ferry boat, museum, golf course, marina, boat rentals, swimming pool, playgrounds. 2 min walk to Joni's beach. Tucked in our beautiful back yard (private to renter, not used by owner) behind the house we live. So close to everything but yet in the quietest part of Main Street. Ideal for families or couples. Max occupancy 4-6. Every person above 4 (approved only by host) is $30.00 a night.

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.

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!

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.

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.

South Shore A-Frame | Steps from Lake Superior

A peaceful, feel good place. Renovated rustic modern A-frame on Lake Superior's scenic south shore. Surrounded by evergreen and birch trees in an idyllic woodland setting. Enjoy walks to the beach, breathtaking sunsets and beach bonfires, kayaking the famous seacaves, biking, hiking to waterfalls, shopping for vintage treasures or just relaxing/stargazing in the beautiful private backyard. A perfect home base for exploring the Apostle islands, Bayfield and Madeline Island.

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.