WELCOME TO OLSON'S.
Classic Lake Michigan Cottages in Door County, WI

Family-owned beachfront cottage rentals where generations return each Summer to make lasting memories by reconnecting with the lake, the beach, the county, and each other.

Located directly on the sand along Lake Michigan, Olson Cottages offers four private, weekly cottage rentals designed for families seeking a traditional Door County vacation. For over 80 years, guests have gathered here for quiet shoreline mornings, afternoon swims, and evenings around the fire.​

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See what Door County Living Magazine had to say about us HERE

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A True Lakefront,
​Door County Cottage Experience

Olson Cottages offers classic Lake Michigan cottage rentals in Door County, Wisconsin. Our four family-owned cottages sit directly on a private stretch of shoreline, providing uninterrupted lake views and immediate beach access.
Unlike large resorts or high-turnover vacation homes, Olson Cottages preserves the traditional Door County rhythm — simple comforts, fully equipped kitchens, lakeside decks, and space to gather. Weekly summer rentals allow families to settle in, unplug, and experience the lake the way it was meant to be enjoyed.
If you are searching for a Lake Michigan cottage rental in Door County that feels authentic, quiet, and deeply rooted in tradition, you’ve found it.

Our "OG DoCo" Cottages

​ TWIN CEDARS COTTAGE
A timeless Lake Michigan beachfront cottage with panoramic water views and private beach access — ideal for families who want to wake up steps from the sand.​

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GRANDMA'S COTTAGE
Built in 1922, Grandma’s Cottage is the heart of Olson’s heritage. Warm, nostalgic, and directly on Lake Michigan, it offers the authentic Door County cottage experience generations have loved.​
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REDWOOD COTTAGE
Recognized by its iconic shutters for decades, Redwood blends classic charm with updated comfort. Perfect for families seeking a traditional Lake Michigan cottage with modern conveniences.

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GREENWOOD COTTAGE
Spacious and welcoming, Greenwood offers a large kitchen and deck designed for gathering. A favorite for multi-generational families who want room to relax while staying close to the shoreline.

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Twin Cedars Cottage photo courtesy of our guest, Sue K.

Family Owned & Operated for 80+ Years

YOUR HOSTS,
​THE OLSON/HASENJAGER FAMILY

MANAGER & RESERVATION AGENT:
Ben Olson - to the right of the plaid shirt - 
(Ben's wife Lisa)
Email: [email protected]

​OWNERS:
Penny Olson and Glenn Hasenjager
(Mr. and Mrs. Glenn Hasenjager) center.

For generations, Olson Cottages has remained a family-owned Door County landmark. Many of our guests first visited as children and now return with their own families — reclaiming the same shoreline, the same  views, and the same summer week each year.

This is not simply a rental property.
It is a Door County tradition.

Our commitment remains unchanged: preserve the simplicity, protect the shoreline, and provide a clean, quiet, welcoming place where families can create lasting memories in Door County.

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Slow Down and Stay Awhile!
​Your Door County vacation at Olson Cottages begins with the sound of waves and ends with the stars over Lake Michigan. Guests enjoy:

• Private Lake Michigan beach access
• Weekly summer cottage rentals
• Fully equipped kitchens for shared meals
• Outdoor decks overlooking the water
• Fire pit evenings beneath open skies
• Quiet lakeside shoreline away from traffic and crowds

Here, mornings are unhurried. Afternoons stretch longer. And evenings invite everyone outside.

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LAKE MICHIGAN COTTAGE RENTALS IN DOOR COUNTY

​Located between Jacksonport and Baileys Harbor, about 20 miles north of Sturgeon Bay, Olson Cottages offers the best of both privacy and convenience. Guests enjoy peaceful Lake Michigan all sand shoreline access while remaining close to restaurants, shops, marinas, and Door County attractions.
For travelers searching:

• Lake Michigan cottage rental Door County
• Beachfront cottages
• Private shoreline vacation rental in Wisconsin
• Classic family cottage on Lake Michigan

Olson Cottages offers a rare and enduring option.

What our recent guests are saying...

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"It was a DELIGHT to stay here at Olson Cottages - What a very special place!"

"Feels like home."

"What a beautiful place!"

"We love it here!"

Welcome to our piece of paradise!

UNPARALLELED VIEWS
PRIVATE BEACH
FIREPLACES WITH FIREWOOD
FULL KITCHENS
SLEEPS SIX GUESTS

OUTDOOR DECKS
​LAKE MICHIGAN BREEZES
EXCELLENT SWIMMING
CENTRALLY LOCATED
​HIGH SPEED INTERNET

VINTAGE.  UNIQUE.  UNFORGETABLE.

 Are Olson Cottages
right for you?

It takes a certain type of person, a mind frame, a willingness to unplug to truly enjoy a week or more at Olson's.  We're a classic beach cottage resort where rest, relaxation, a good book, a long swim, an evening fire and time with those you love are the greatest pleasures you'll enjoy. 
PLEASE NOTE THAT PETS ARE
​NOT ALLOWED AT OUR COTTAGES.
If you want to get away from it all, this is your place.  If you'd rather have a full-service resort with all the amenities, perhaps you should look elsewhere. Please be sure to visit our About Us page to learn more about what is and isn't included in your vacation time at Olson Cottages. Naturally, we hope you will enjoy our unique piece of Door County, but we'll understand if we're not your cup of tea!

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FULL DETAILS AND RATES

Want to get in touch?

Our reservation process begins the previous Fall with preference given to our existing guests. 
Please contact us via the form below for more information and for reservation inquiries. 
We'll get back to you in the order of inquiry and as quickly as we are able.

BEGIN YOUR RESERVATION

Olson Cottages, LLC
​6852 STATE HIGHWAY 57
BAILEYS HARBOR, WI 54202
45°00'22.5"N  87°09'44.6"W

RESERVATIONS:
(920) 495-2365

EMAIL US

​Classic Lake Michigan cottage rentals in Door County. Family-owned beachfront cottages near Sturgeon Bay with private shoreline access and weekly stays.