Stay in a Historic Schoolhouse 15 minutes to NU!


Entire guest suite hosted by Nancy

  1. 2 guests
  2. 1 bedroom
  3. 2 beds
  4. 1 bath
Dedicated workspace
A common area with wifi that’s well-suited for working.
Self check-in
Check yourself in with the keypad.
Nancy is a Superhost
Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.


Every booking includes free protection from Host cancellations, listing inaccuracies, and other issues like trouble checking in.
It really was a Montessori schoolhouse! The famous teacher lived in your upstairs apartment.
You are fifteen minutes to Northwestern and forty minutes to downtown Chicago with the train and bus on the same block.
This is a child-friendly stay-your host has everything you need to keep the kids busy.

The space
You really are staying in the founding teacher’s living quarters of the North Shore Montessori Schoolhouse! This second floor 1 BR apartment is just fifteen minutes to Northwestern and forty minutes to downtown Chicago, with the convenience of public transportation so you really don’t need a car!
You’re also a ten minute walk to our beautiful Lake Michigan beach, a one minute walk to the CTA and UPN Metra line, our quaint downtown village shops, restaurants, upscale shopping, a walking path, grocery stores and banks.
You are above my living quarters in the second floor apartment with a private entrance, outdoor deck, and designated parking in the driveway.
You will have a meticulously tidy kitchen and full bath. I am a vintage dealer in decor and women’s accessories and added my personal touches to your abode.
I’m taking not just coronavirus, but all potential pest infestations very seriously and your stay reflects this: cleaned, sanitized, exchanged duvets and pillows that are heat-treated between guests...UV-C light treatment in each room to sterilize anything that could have been missed; and bed bug traps on the bed legs.
On the luxurious side of your stay, lavender infused Turkish towels, Anthropologie linens and special amenities like Keurig coffee pods, gift basket, and a DIY popcorn bar are offered.
For you history aficionados: Dorothy Sears was the daughter of Joseph Sears. Joseph Sears was the founder of the affluent town just south of Winnetka named “Kenilworth.” Legend has it that Dorothy not only taught Montessori, but she also hosted interracial tea parties. I love her spirit! Her father was known to be a racist. Our Winnetka Historical Society is a block from your stay-you can reserve a time to visit and see the archives. I also provide the pages from the schoolhouse promotional flyer.
I’m honoring the era by returning the yard spaces back to prairie gardens and native plants as much as possible.

Where you'll sleep

What this place offers

Courtyard view
Lake access
Dedicated workspace
Free parking on premises
HDTV with Apple TV, Amazon Prime Video, Hulu, Netflix, Roku, standard cable
EV charger
Paid washer – In building
Security cameras on property

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4.89 out of 5 stars from 66 reviews


Where you’ll be

Winnetka, Illinois, United States

You’ll be in one of the best towns in the most beautiful location in all of Illinois! Winnetka was just voted “best suburb to live in in Illinois.” It boasts many famous celebrities, wealthy socialites and heads of major corporations and professional sports teams. It is serene.

Parents move here to raise their children because of the fantastic schools, safety, commute and walkability score to every amenity imaginable.
Below I’ve listed a few places within two blocks of the apartment to Shop, Dine, and Site-See. Your in-room guidebook has more….

You and your children can use the driveway or walk across the street to the church parking lot or one of our several parks to play basketball, wiffle ball, badminton, or corn hole! I have the equipment.

For our most current retail, services, and restaurants, visit our Winnetka-Northfield Chamber of Commerce website. I included a sampling below!

WEST SHOPPING DISTRICT DINING (one block north on west side of Green Bay Road):
-Avli Restaurant-Amazing Greek food!
-Green Bay Cafe-fantastic breakfast and lunch served. Cash only.
-Fred’s Garage-lunch and dinner. American.
-La Taquiza-the real deal for Mexican.
-Tocco. Same owner as the Chicago locale. High-end Italian dining.
-501 Local. American.

-Bake 425 for take-and-bake pizzas and salads.
-Mirani's At Home-fantastic fine dining that's take-home only!
-Stacked and Folded-tacos, salads, and sandwiches

(Further North, there’s Hubbard Woods and Glencoe which has even more fabulous eats and shops, but it’s not within walking distance)

Local Groceries:
-The Grand on Green Bay and Spruce.
-Lakeside Foods-enter on Chestnut Court or Elm Street (in between Green Bay Road and Chestnut).

-Chase Bank: NW corner of Elm/Green Bay (West shopping district)
-Chase ATM: Spruce just west of Green Bay Road (Just west of The Grand grocery store)

Saturday Farmers’ Market (May-October)
(7 AM - Noon)
Northwest corner of Linden/Green Bay and Oak Street (just northwest of the house).

There are jewelry stores, a toy store, bike shop, spas, nail salons, yoga, pilates, and so much more! We are a very health conscious town! It's best to check our full list of businesses at our chamber of commerce sites in nearby towns of Winnetka, Northfield, Glencoe, and Wilmette!

-Lloyd Beach - for renting kayaks, SUP, or launching your boat! Be a guest for just $20 at Lloyd Beach and rent a SUP!
-Tower Road Beach

*Our library is on my same block. If you need something printed for free, head there! There’s also a new attractive outdoor patio on the north side of their building…great children’s library, too. Check out The Studio in the basement for a NEW FREE craft project every week...or get a tutorial on the embroidery machine or 3D laser printer-you only pay for materials and all are welcome.

Hosted by Nancy

  1. Joined in February 2016
  • 66 Reviews
  • Identity verified
  • Superhost
I used to travel extensively for Discovery Channel. Hotels got to feel sterile and impersonal. That said, I fell in love with the charm of B & B’s, the hosts, the locals, and all they had to share about their area and their lives!
I’m so fortunate to be able to share my love of B&B’s, my town and its locals, my vintage decor and more!
My past has led me on this path and my dream has become a reality: I am a former Glencoe Junior High School science/technology teacher, the former president of the Winnetka’s Village Club of Newcomers, a former Winnetka Chamber of Commerce member and store owner.
I have two fantastic kids and a guinea pig, all of whom are excited to meet you (well, maybe not the guinea pig?! It’s hard to tell-he’s not very emotive!).
We look forward to welcoming you to our neck of the woods, our ‘hood we call Winnetka!
I used to travel extensively for Discovery Channel. Hotels got to feel sterile and impersonal. That said, I fell in love with the charm of B & B’s, the hosts, the locals, and a…

During your stay

I’m a very social, gracious and welcoming person-the perfect hostess!
I understand the need for privacy and quiet, so I will take my cues from you.

Nancy is a Superhost

Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.
  • Languages: English, Español
  • Response rate: 100%
  • Response time: within an hour
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Things to know

House rules

Check-in: After 4:00 PM
Checkout: 11:00 AM
Self check-in with keypad
No smoking
No pets
No parties or events

Health & safety

Airbnb's COVID-19 safety practices apply
Security camera/recording device Show more
Climbing or play structure
Carbon monoxide alarm
Smoke alarm

Cancellation policy