Winnetka Vacation Rentals

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Browse Select Winnetka Vacation Homes

"Very nice place "

CA $323 total

includes taxes & fees

Aug 11 - Aug 12

"Very nice and newly remodeled property. Would definitely recommend. Property owner was pleasant and attended to maintenance issues promptly. Pool table and air hockey tables were fun to play on. There is even a sauna on the property but we did not use it. Great location for being near the Naval base."

Relax in a spacious room with high ceilings and large windows, featuring a comfortable seating area and a crib for a family-friendly stay.

"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."

Desk, iron/ironing board, free WiFi, bed sheets

"We had a fantastic stay! The property was perfect for kids — safe, clean, and had plenty of space to play. The outdoor space is perfect for morning coffee, lounging, afternoon cocktails, and dinner under the stars. This location was unbeatable, close to everything we wanted to do. Couldn’t have asked for a better spot for a family getaway in the city. Highly recommend!"

Enjoy cooking in this well-equipped kitchen with a coffee maker and ample countertop space.

"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "

Enjoy cooking in this well-equipped kitchen with a large island and oven.

"Only complaint was the fact that the yard was not cut and the grass needed to maintained"

CA $626 total

includes taxes & fees

Sep 9 - Sep 10

Sit on the porch and enjoy the serene surroundings.

"Great house,great location,close to a lot of attractions and bars. Owners was egged to help and responded quickly to all our questions "

CA $773 total

includes taxes & fees

Aug 13 - Aug 14

Enjoy cooking in this well-equipped kitchen with a microwave, oven, refrigerator, and dishwasher.

8 bedrooms, desk, iron/ironing board, travel crib

CA $1,260 total

includes taxes & fees

Aug 12 - Aug 13

4 bedrooms, iron/ironing board, free WiFi, bed sheets

"Excellent location, right by the zoo, the place is well stocked and clean, in a nice neighborhood. Close to attractions and easy to go to other western suburbs of Chicago. Has everything we needed :). The host was great with communicating and was able to allow us to borrow a pack n play as well. Would stay again! "

CA $893 total

includes taxes & fees

Aug 10 - Aug 11

Enjoy cooking in this well-equipped kitchen with a stainless steel sink, coffee machine, and microwave.

"Everything was as it was described. Very nice "

Stunning single-family home with a backyard surrounded by mature trees and a well-manicured lawn.

"Comfortable beds and room for everyone. Nice quiet neighborhood and a great home away from home. Would stay there again. Host was very easy to work with and responded quickly to questions. "