Search Condo Rentals in Winnetka

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 244 Condo Rentals in Winnetka with updated reviews, rates, and availability.

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (88)
"A clean, spacious, affordable option in a perfect location in Lincoln Park. Plan to return in the future."
Stunning 3 BR in prime Chicago location

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (170)
"Very clean, property manager was very nice and helpful. Close to everything. Would definitely stay there again. "
NEW LUXURY PENTHOUSE CONDO

Historic Gold Coast Condo - Half Block From Beach & Major Attractions

Historic Gold Coast Condo - Half Block From Beach & Major Attractions

Pet-Friendly Urban Chicago Vacation Rental Condo

9.2 out of 10, Wonderful, (14)
"Great place to stay. Close to everything. Nice and clean "
Pet-Friendly Urban Chicago Vacation Rental Condo

Experience Chicago living near United Center -

9.2 out of 10, Wonderful, (24)
"overall place is good, the only bad thing is the location!"
Experience Chicago living near United Center -

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (27)
"Specious and comfy. The balcony was not available, but we just needed the place for a few nights. Clean and nicely done"
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

10.0 out of 10, Exceptional, (22)
"We were visiting our nephew, who lives around the block from this rental, so we didn't spend a lot of time in the rental, but it was absolutely sparkling clean, well-appointed, and lovely. We will definitely book it again. "
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (64)
"I lived in Chicago for years and this was the first time I brought my son. It was exactly what I was hoping for. Walk up in an old building, restaurant on the bottom floor, transit a quick walk away."
Classic Lincoln Park 2 bedroom condo- parking included

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.4 out of 10, Exceptional, (25)
"It has been for us the perfect place to visit the city and enjoy an amazing neighborhood. The parking spot makes it even more perfect. Great communication from the property manager on top of that"
3BR Modern Condo near Wrigley/Dwtn +Free Parking

North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment

10.0 out of 10, Exceptional, (102)
"Really enjoyed our stay. Parking was easy and we could walk to restaurants. Felt very safe and the neighborhood was welcoming. Would stay again."
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment

Wrigleyville Inn - Garden Unit

10.0 out of 10, Exceptional, (24)
"My husband and I drove in to surprise our oldest for her birthday. The space was very clean and comfortable as well as ideally located next door to her home. We would definitely consider staying her again in the future. "
Wrigleyville Inn - Garden Unit

Experience Chicago living near United Center

9.4 out of 10, Exceptional, (13)
"Everything was as advertised. Neighbors with dogs barking in the night and car honking/other outside elements can be disruptive if you're a light sleeper. Very quick and fast communication with host even at 2am. Would recommend."
Experience Chicago living near United Center

Gorgeous 3BR River North Condo - Free Parking

10.0 out of 10, Exceptional, (11)
"This condo is absolutely beautiful, very posh! Upscale designs, looks exactly like the pictures! Very clean! My family and I were very pleased! Now, just for info, if your traveling with an elderly or a person with restricted mobility, the full bathroom on the main floor has a very high shower/bathtub combo, thats enclosed with glass doors...getting in and out of that tub/shower can be challenging...there is another full bathroom downstairs, just note the stairway leading to it is very...
Gorgeous 3BR River North Condo - Free Parking

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (156)
"This is the perfect place for you to stay when you’re in Chicago. We have stayed here at least four or five times already the place is immaculate. If you need any help someone is there for you ASAP. "
NEW LUXURY CONDO WITH PATIO DECK

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (10)
"The property was nice. It had everything we needed, close to a store, restaurants and the train. "
The price is AED 551
AED 1,628 total
includes taxes & fees
30 Mar - 31 Mar
Chic Urban Retreat Near Wrigley Field w/Parking

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

10.0 out of 10, Exceptional, (88)
"Property perfectly located near Wrigley Field, superbly clean and appointed."
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.6 out of 10, Exceptional, (25)
"The place was super nice, very clean, and quiet. It was perfectly located for our needs. We were visiting my daughter and brand new granddaughter, and hope to make it our new home away from home when we visit."
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

Chicago Condo: Near Lincoln Park & DePaul!

9.6 out of 10, Exceptional, (8)
"You can't beat the location, the street is lovely and quiet and close to public transit, Lincoln Park, shopping, etc. The condo is small but well appointed and clean. (There wasn't soap/shampoos so pack accordingly : )). Overall a lovely place in a great location. "
Chicago Condo: Near Lincoln Park & DePaul!

Spacious Wicker Park Hideaway with Parking!

8.8 out of 10, Excellent, (6)
"Very clean with new appliances, cute kitchen and beds were comfy. The location was perfect for visiting our Wicker Park family. Walkable neighborhood. Drove or ubered to the downtown sites. Lots of restaurants and bars nearby. The host was very responsive. Overall great visit. to any questions. "
Spacious Wicker Park Hideaway with Parking!

Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago

9.8 out of 10, Exceptional, (12)
"Everything went well. Will stay again."
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Winnetka
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winnetka

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (706)
"We love coming here and we come at least once a year. My only thing is we always get the lake side and this time we did not. Still a nice chicago skyline view but if you can get the lake side it’s gorgeous!"
The price is AED 465
AED 654 total
includes taxes & fees
20 Apr - 21 Apr
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (454)
"As advertised. Would stay again. "
The price is AED 345
AED 405 total
includes taxes & fees
20 Apr - 21 Apr
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (267)
"It was good. Booking, arrival, and departure were easy. Bed was ok. Everything was clean and smelled nice. Parking was not easy and had to walk quite a distance. I don’t recall seeing that being the case when booking. "
The price is AED 392
AED 460 total
includes taxes & fees
22 Apr - 23 Apr
Sonder Market Hall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do condos in Winnetka cost?
Condos in Winnetka range from AED 551 to AED 551 per night. This will give you lots of room for your entire crew at a price that won’t stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Winnetka?
Choose from 244 condos in Winnetka. Whether you’re traveling with the family or organizing a weekend break with your buddies, Expedia can help you find the right space for your whole crew.
Why book your condo in Winnetka with Expedia?
Expedia will help you find your ideal condo in Winnetka. After a luxury escape? Make the most of our filters to search for properties that have a 5-star rating. If you’re sticking to a budget, select how much you want to spend and then browse our fabulous options. We’ll help you find the right place whatever your vacation looks like.
How can I find cheap condos in Winnetka?
The best way to locate cheap condos in Winnetka is with Expedia’s nifty filter tool. Fine-tune your search results by amenities, budget and star rating to secure unbeatable rates in a couple of clicks.