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

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

Welcome to Olson's
We have no availability for 2022.  If you are interested in 2023, please visit our contact us page and submit your request. 
​Scheduling is done in December and January

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.

A NOTE ABOUT LAKE MICHIGAN
While Lake Michigan recently hit an all-time record high just 2 years ago, it has been steadily going down over the last 2 years.  As such, our beach is returning nicely.  We still are not back to the days of beach fires, but a fire pit is provided for our guest's use on our hill overlooking the lake and our decks still offer unparalleled views.   Please note that some photos on this website were taken during lower levels.
2022 above, 2021 below
What a difference 22 years can make!
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. 

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)

HONEYMOONING ​AT OLSON'S
The Olson family has a long history of welcoming newlywed couples on their honeymoons.  Our cottages offer a warm, cozy, romantic atmosphere that provides a great place to relax after your big day and begin your new life together.

Twin Cedars and Redwood Cottages have been longtime favorites and we urge you to look at their features and consider them for your honeymoon.  Great weeks in Early June and September are available in 2020.

Contact us today to check availability at olsoncottages@outlook.com
Our tradition of being a honeymoon destination goes back to our original "Honeymoon Cottage" shown here in the late 1920's on the right.  Later, this cottage was replaced by Twin Cedars in the early 1960's, with that cottage becoming our unofficial honeymoon cottage.
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.
For Your Consideration: 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 few days 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 the kingdom so delicious, Door County in the Autumn of the year.  

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