Monthly Rentals in Winnetka

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Top guest favorite
Townhouse in Winnetka
4.95 out of 5 average rating, 41 reviews

Warm and Cheerful 3 Bedroom Winnetka Townhouse

RosemaryRating, 5 stars1 month ago
This was our fifth stay at Gabriel and Glaucia's property. We love coming to this property because it is comfortable, inviting, and allows each of us space to work and relax. The kitchen is outfitted well for cooking. Their property is always immaculate, and Gabriel is quick to respond to any questions. It is in a most convenient location. Having a garage is especially convenient. Highly recommended ~ and we'll definitely come back!
Top guest favorite
Home in Highland Park
4.91 out of 5 average rating, 65 reviews

A Wonderful Getaway Home on the North Shore!

KathyRating, 5 stars1 month ago
Wow, what a wonderful home! It really felt like home--comfortable and beautifully decorated. We appreciated a lot of the amenities including high quality towels and the most comfortable sheets! Phil is very personable and super responsive. The house itself is in a quiet neighborhood within walking distance to the town of Ravinia and the train station. We can't say enough about how much we enjoyed our stay. Thanks, Phil!
Superhost
Apartment in Wilmette
4.88 out of 5 average rating, 34 reviews

The Shop - Trendy Studio in the heart of Wilmette

MichaelRating, 5 stars3 weeks ago
This was my second stay at The Shop. It's a favorite for me, as it's perfectly located in Wilmette, with easy access to restaurants, the train and other shopping. The place is super clean, super comfortable. Hosts (Rick and Anna) are great at communicating and making my stay the best. I'll stay again, if I can.
Top guest favorite
Home in Wilmette
4.98 out of 5 average rating, 144 reviews

Unique porcelain-enamel paneled "Lustron" home

LianaRating, 5 stars1 month ago
David’s house is hands down the best Airbnb we’ve stayed in! The home is beautiful, peaceful, and incredibly private, with an amazing backyard that made our stay even more special. From the moment we walked in, it felt like home—cozy, well-stocked, and thoughtfully designed for guests. He provided firewood for the fireplace, all the toiletries, amenities, and an incredible selection of cooking utensils and spices. You could arrive with just your clothes and be completely set. David is an amazing host—super responsive, thoughtful, and went above and beyond to make sure we had everything we needed. If we asked for something, he got it for us right away. He truly cares about the guest experience, and it shows in every detail. This place is a rare gem, and we can’t recommend it enough!

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

Stay near Winnetka's top sights

Writers Theatre8 locals recommend
Starbucks8 locals recommend
Historic Wagner Farm5 locals recommend
Glencoe Beach4 locals recommend
Graeter's Ice Cream3 locals recommend
Winnetka3 locals recommend
*Some exclusions may apply in certain geographies and for some properties.
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