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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 230 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, (94)
"We fully enjoyed our stay - location, space, communication were all excellent!"
Stunning 3 BR in prime Chicago location
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (176)
"This property was great, would definitely return sometime. Has everything you need and then some. Property management was very easy to work with."
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
Urban Chicago Vacation Rental Condo Near Beach!
Beach nearby

Urban Chicago Vacation Rental Condo Near Beach!

9.2 out of 10, Wonderful, (18)
"Great place to stay. Close to everything. Nice and clean "
Urban Chicago Vacation Rental Condo Near Beach!
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, (32)
"It was a great place to stay and very spacious!"
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, (24)
"Great experience. "
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, (67)
"We had a great stay at the rental. Stacy was an amazing host. We would definitely stay there again. "
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

9.4 out of 10, Exceptional, (30)
"Easy check in and lovely stay- thank you!"
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, (105)
"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
Fridge, microwave, oven, stovetop

Wrigleyville Inn - Garden Unit

10.0 out of 10, Exceptional, (26)
"The garden apartment was perfect for our family gathering. The location is convenient and in a nice neighborhood. The layout provided all of us privacy when we needed it and plenty of room for celebrating! "
Wrigleyville Inn - Garden Unit
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center

9.2 out of 10, Wonderful, (15)
"The place was amazing. The area is questionable but we didn't experience any problems while we stayed. "
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, (13)
"This spacious condo was perfect for our family of 7. Having a parking spot was a huge help and the location was incredibly convenient for use of public transport throughout our stay. We'd definitely stay there again!"
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, (158)
"Very nice property—definitely would stay again"
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, (14)
"Great location near Southport corridor between two nearby stops on brown line. Good living space and clean. Host provided clear information about check-in and check-out with an information binder of nearby attractions. "
The price is $447
includes taxes & fees
$440 per night
May 4 - May 5
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, (91)
"Great location and condo will definitely be back !"
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)
"What a great place! Perfect for a stay close enough to everything! Very comfy beds, and couch (tv remote was literally the only thing I can complain about!)"
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)
"Great neighborhood on a quiet street. The floors are a bit squeaky but otherwise the stay was pleasant and the apartment was lovely."
Chicago Condo: Near Lincoln Park & DePaul!
Spacious Wicker Park Hideaway with Parking!
Fridge, microwave, oven, stovetop

Spacious Wicker Park Hideaway with Parking!

8.6 out of 10, Excellent, (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, (13)
"The place was clean and spacious. I appreciated the parking space which made unloading the car to the apartment super easy. Communication from the host was helpful and check-in was a breeze. Would 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, (737)
"Great family place to stay. "
The price is $188
includes taxes & fees
$160 per night
May 1 - May 2
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, (484)
"Great stay "
The price is $132
includes taxes & fees
$112 per night
May 26 - May 27
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (277)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is $152
includes taxes & fees
$129 per night
May 26 - May 27
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 $447 to $447 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 230 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.