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Welcome to Olson's​
2023 availability includes prime weeks in Greenwood Cottage

Olson Cottages are one of
Door County's
last unspoiled treasures.

Olson Cottages are four vintage housekeeping cottages nestled on Lake Michigan available for weekly rentals (long weekends in Fall) for your family vacation, your honeymoon, your family reunion, a quiet retreat or a romantic getaway for 2.  In fact, we’ve been welcoming vacationing families to our beach for 80 years. 

Our Unique Cottages

 TWIN CEDARS COTTAGE
Twin Cedars sits right on the lake and features 3 bedrooms (sleeps 6) along with a log cabin interior, field stone fireplace, open kitchen/dining and living room and a great sun deck.
GRANDMA'S COTTAGE
A Door County Classic!  Log cabin with 3 Bedrooms (sleeps 6), Wrap around, glassed-in porch, double height living room with stone fireplace - this was our family's original cottage and will celebrate 100 years in 2022.
​
REDWOOD COTTAGE
A Perennial Favorite!  Redwood features 3 bedrooms (sleeps 6), cathedral ceilings with log beams, charming kitchen with deck access and a great view and fireplace.​​​​​
GREENWOOD COTTAGE
Greenwood features 2 bedrooms (sleeps 6) and a beautiful knotty pine interior, including a large, custom  kitchen. Greenwood has the largest kitchen and bathroom of all of our cottages. Greenwood has limited lake views but full beach access. 
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 - center left, in brown pants  
Email: olsoncottages@outlook.com

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

RELAX & ENJOY!
​Our lake front cottages each offer decks and outdoor spaces and the sound of the waves will help you slip into relaxation mode.  While our beach may currently be experiencing high water, dipping you toes, or a great swim in Lake Michigan is still a simple pleasure.

At Olson’s, you won’t find many of today's distractions.  Here, a day of activity can be followed by a family or romantic evening in front of the fire.  It’s a simpler kind of vacation, a chance to unwind and relax, yet Door County activities such as shopping, biking, exploring, theater, dining and golf are just a short drive away. 

Each of our housekeeping cottages sleep 6 in different bedroom/bed size configurations. (see our individual cottage pages for complete details).  All feature kitchens with microwaves, central heat, bathrooms with showers and firewood for the fireplaces and fire pit.  Guests are responsible for bringing their own linens and supplies.  For 2020 we have added Wi-Fi for limited checking of emails and web surfing (limited bandwidth does not permit streaming)

We're a small, family owned and operated resort with on-site owners and direct reservations.  No absentee ownership or management, or additional fees to large booking agents.

Our classic cottages are situated on Lake Michigan and the sounds of the waves provide the perfect backdrop for a vacation to remember. 

For Your Consideration in 2023
GREENWOOD COTTAGE
Your Lakeside Cabin in the Heart of Door County
For the 2023 season, Greenwood is the only cottage available during most of June, July, August & September

Warm. Comfortable. Affordable.

Like all of our cottages, Greenwood is located almost exactly in the center of Door County, on the 45th parallel, exactly 1/2 way between the equator and the north pole. 
​Our location puts you minutes away from all Door County has to offer.
Greenwood Cottage sleeps 6 in 2 bedrooms.​

In 1922, Albert & Arlouine Tressler had Grandma's Cottage built.

Today, the third, fourth, fifth and sixth generations recently celebrated 100 years of Grandma's Cottage

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
​Wi-Fi (Limited Bandwidth)
OUR UNIQUE PROPERTY

 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.  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.
Autumn at Olson Cottages
The beach is almost empty.  The children are back in school.  The days are still long and bright.  Door County’s finest shops and restaurants are open and ready to serve you.  Tee times are easier to get at the county’s wonderful courses.  The trails at the state parks are less crowded.  It’s September in Door County and Olson Cottages is as welcoming and appealing, if not even more so, than during the months of Summer.
The weather may well still allow beautiful days on the deck and long walks on the beach.  Nights are toasty by the fire and the efficient central heat makes shivers a thing of the past.  No matter which cottage of ours you choose, you’ll enjoy a week at our secluded private beach in a cottage weathered by time and steeped in tradition.
As October approaches, green turns to crimson, gold and russet, mixed with the evergreen of pines and hemlock.  The lake is cold, but the beach still inviting, the shops still open, the state parks and lighthouses still a delight and the golf courses, theaters and restaurants still irresistible.  As Sister Bay’s Fall Fest gets closer, perhaps a long Columbus Day weekend or a quieter week at our special family cottages is in order?
A relaxed pace prevails in the Autumn, but don’t let that keep you from reserving your cottage now for an unforgettable time in what National Geographic calls, "The kingdom so delicious."  Door County and Olson Cottages in the Autumn of the year - a great combination.  

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.
Olson Cottages, LLC
​6846 STATE HIGHWAY 57
BAILEYS HARBOR, WI 54202
45°00'22.5"N  87°09'44.6"W
RESERVATIONS:
(920) 495-2365