When we first met with Olson Cottages, we saw how the property stretches over 340 feet of Lake Michigan shoreline. And each of the four cottages here in Baileys Harbor has its own dedicated sitting area on a private beach—a firepit and five Adirondack chairs. 

Olson Cottages have quietly sat on Door County’s lakeside for decades. The current owner, Penny Olson, has taken good care of the cottages, updating them with new windows, exterior painting, decks, septic systems and more.

In addition to her long-time family connection to the cottages, also special here are the preservation of architectural details as well as the pristine setting on  Lake Michigan.

In fact, three of the four cottages, sit just about 30 feet from the beach.  The views are lovely from the living rooms, and the sound of the waves from the bedrooms is so restful and nourishing.  A fourth cottage has a limited lake view from its kitchen and deck.

All four cottages each have one bathroom, an outdoor deck/patio and fully equipped kitchen.

Your choices at Olson Cottages are the following:

Redwood Cottage: a three bedroom and one bathroom cottage built in the mid-1930s with a major renovation in 2003 that updated windows, kitchen, added the deck and more.

What’s so lovely—if you adore vintage details—is open shelving in the kitchen, where pretty blue pottery brightens the room. Nearby is an old farmhouse table.

Step into the living room and be captivated by the intimate view of the lake through the big window. The pitched high wood ceilings are a focal point and perhaps an architectural feature you might not expect.  Also, don’t miss the native stone and quartz wood-burning fireplace.

“When we redid the cottages, we wanted to keep the flavor of Door County and have something for families,” Penny said.  “This is about an old Door County experience—to see Door County the way it was.”

Twin Cedars Cottage: This is a genuine log cabin, offering three bedrooms and one bathroom to travelers.  The natural logs and intriguing ceilings will catch your eyes to be sure.

Kids will love the bedroom with bunk beds; the beds are nestled near the window, too, offering a view of the water and sound of the waves. 

Grandma’s Cottage: Built in 1922, this is the first Olson Cottage and offers three bedrooms and one bathroom today. It is also the first log cabin to be built on the beach, Penny explains.

Showstoppers here include the spacious living area with the natural log walls and original stone fireplace and birch mantel.  Adjacent to the living room is an indoor sunroom which stretches across the cottage. There are a number of seating areas in the sunroom—all offering the pristine view of the lake.

Greenwood Cottage has two bedrooms and one bathroom. It has a limited lake view from the kitchen and deck.

The owner likes to recommend that people enjoy the beach before noon, because the wind will shift. Then, she advises heading over to other areas of Door County. Her tips include playing golf at the Red Putter. 

She takes good care of the cottages, even cleaning the natural log and wood walls each year. The cottages are fresh and welcoming. 

Olson Cottages will appeal to people who appreciate authenticity, value and serenity. If that is you, give Olson Cottages a call, and tell them DoorCountyNavigator.com referred you.

Features at a glance:

Four cottages on the beach

Vintage and architecturally intriguing log cabins/cottages

Private bathroom with shower in each cottage

Fully equipped kitchen with stove, refrigerator, microwave, toaster, coffeemaker pots and pans, dishes

Beachfront sitting area

Gas grills, campfire pits

CD players/radios