Monthly Rentals in Winnetka

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

Nearby monthly rentals

Top guest favourite
Home in Northbrook
4.97 out of 5 average rating, 65 reviews

*King bed *Outdoor Living *Sought-After Area

ChristineRating, 5 stars2 days ago
The house was so clean, beautifully decorated & has a homey feel. Elizabeth communicated timely & was very helpful. The neighborhood felt safe & has lots of restaurants, shopping & even a botanical gardens nearby.
Guest favourite
Apartment in Evanston
4.96 out of 5 average rating, 94 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

PeteRating, 5 stars3 days ago
This condo is well appointed and stocked with coffee, creamer and seasonings. The building has a nice common area with fancy coffees and a decent work out room. We love the location near downtown Evanston and the public transportation to Chicago. We’ve stayed here many times and plan to stay here for all our Chicago visits.
Top guest favourite
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 favourite
Home in Wilmette
4.98 out of 5 average rating, 144 reviews

Unique porcelain-enamel paneled "Lustron" home

LianaRating, 5 stars4 weeks 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 holiday 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

Travelling 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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