Search Condo Rentals in Winnetka

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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

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

Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (88)
"Accurate description of property. Host was very easy to communicate with. Would recommend!"
Stunning 3 BR in prime Chicago location
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

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
Interior

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
Beach nearby

Pet-Friendly Urban Chicago Vacation Rental Condo

9.2 out of 10, Wonderful, (15)
"This apartment was so cute, quiet and a great stay for my family and I. The host was able to accommodate extra blankets and towels for us during our stay. As well with it being a pet friendly property our dog enjoyed his stay and a little bit of the city life. Dinner is walkable as well as access to the main transit system. This is definitely a good spot for a girls trip or even a single that wanted to different kind of stay in Chicago!"
Pet-Friendly Urban Chicago Vacation Rental Condo
Experience Chicago living near United Center -
Fridge, microwave, oven, stovetop

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
Exterior

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
2 bedrooms, iron/ironing board, WiFi, bed sheets

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
Point of interest

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
Miscellaneous

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.6 out of 10, Exceptional, (27)
"I stayed here with my friends for my bachelorette weekend. We all had such a good time. It was a comfortable stay, the furniture was cute and clean. We had plenty of space. The beds and mattresses and pillows were so comfy. The listing was exactly as displayed online. Highly recommend!!!"
3BR Modern Condo near Wrigley/Dwtn +Free Parking
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Exterior

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

10.0 out of 10, Exceptional, (103)
"We absolutely loved staying at this property. We stayed with three children under the age of 5 and everything we could have thought of for our kids was there. My kids especially loved the sparkles in the tub and some of the toys in the apartment. The host did a great job of recommending places we could go and checking in to make sure we were doing okay. The location is great, within walking distance to the train and great parks. Would recommend this spot to anyone witb families looking to...
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Wrigleyville Inn - Garden Unit
Fridge, microwave, oven, stovetop

Wrigleyville Inn - Garden Unit

10.0 out of 10, Exceptional, (24)
"The location to Wrigley Field and public transit was great! Cleanest place we’ve ever stayed. The only downside was the very raucous upstairs neighbors who like to karaoke late at night on the weekends."
Wrigleyville Inn - Garden Unit
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

Gorgeous 3BR River North Condo - Free Parking

10.0 out of 10, Exceptional, (12)
"George was such a lovely host - very communicative, polite, and helpful. The condo itself was so awesome: extremely clean, furnishings were lovely, and just such a great space overall. We had a total of 8 adults stay, and we all fit very comfortably. Would definitely stay here again with a group!"
Gorgeous 3BR River North Condo - Free Parking
NEW LUXURY CONDO WITH PATIO DECK
Fridge, microwave, oven, stovetop

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
Miscellaneous

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (10)
"This was a great home base for our short family getaway to Chicago. Perfect amount of space for family of 4 to crash at the end of each day touristing around Chicago. Very clean. Great communication from hosts. Loved it."
Chic Urban Retreat Near Wrigley Field w/Parking
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Smart TV, fireplace, printers

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
Fridge, microwave, oven, dishwasher

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!
Fridge, microwave, stovetop, coffee/tea maker

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!
Fridge, microwave, oven, stovetop

Spacious Wicker Park Hideaway with Parking!

7.8 out of 10, Good, (7)
"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
Smart TV

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

9.8 out of 10, Exceptional, (12)
"My family had a long visit to Chicago and this apartment was perfect! It looks just as it appears in pictures. Very comfortable! We hope to stay here 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.
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Other property types in Winnetka

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (710)
"Our family celebrated Christmas at this hotel. It was beautiful and clean. I will definitely stay here again."
The price is SAR 521
SAR 722 total
includes taxes & fees
6 Apr - 7 Apr
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (456)
"Great!"
The price is SAR 412
SAR 483 total
includes taxes & fees
6 Apr - 7 Apr
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (267)
"It is in excellent walking distance from transportation. It is very quiet and the rooms were comfortable. "
The price is SAR 400
SAR 470 total
includes taxes & fees
23 Apr - 24 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 to 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.