Title: Winnetka Vacation Home Rentals from CA $269: Search Top Private Vacation Homes for Rent | Expedia.ca [Winnetka Travel Guide](https://expedia.ca/Winnetka.dx175751)[Hotels in Winnetka](https://expedia.ca/Winnetka-Hotels.d175751.Travel-Guide-Hotels)[Vacation Rentals in Winnetka](https://expedia.ca/Winnetka-Vacation-Rentals.d175751.Travel-Guide-VacationRentals)[Flights to Winnetka](https://expedia.ca/Cheap-Flights-To-Winnetka.d175751.Travel-Guide-Flights)[Winnetka Car Rentals](https://expedia.ca/Car-Rentals-In-Winnetka.d175751.Car-Rental-Guide)[Winnetka Vacation Packages](https://expedia.ca/Winnetka.d175751.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - 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May 10](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America®ionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America®ionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America®ionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America®ionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VACATION_HOME) Villas [](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America®ionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America®ionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=COTTAGE) Residences [](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America®ionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=RESIDENCE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinnetka-Private-Vacation-Homes.d175751-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinnetka-Private-Vacation-Homes.d175751-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winnetka Hotel Reviews ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Very nice, check-in and check out fast and efficient. Staff very helpful and welcoming " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg) ### LondonHouse Chicago, Curio Collection by Hilton 10/10 Excellent "Clean accommodations and friendly staff." [](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "The room was clean. The staff was friendly. The breakfast was not great, but not bad. " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "Our stay was A+, the staff was courteous and helpful and always went above and beyond in service. The location was great across from the Riverwalk and central to many other Chicago attractions. We will be back!!" [](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Nice size rooms, accommodating check in help, and great location " [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "Very good " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Great location. Hotel was clean and comfortable. Staff were very friendly and welcoming. Only problem is that I paid for parking ($92) with my reservation thru Hotels.com and now I see on my credit card that the hotel also charged me for parking. Now I have to fix that problem. " [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "Girls trip / business meeting " [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Great staff, nice pool and big room! " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ## Find out more about Winnetka ## Winnetka Vacation Homes information | Number of reviews | 364 | | ----------------- | ------------------ | | Accommodation | 583 Vacation Homes | | Lowest Price | CA $269 | | Highest Price | CA $1,236 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [5 Star Hotels in Glenview ](https://www.expedia.ca/5Star-Glenview-Hotels.s50-0-d8006.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Gross Point ](https://www.expedia.ca/5Star-Gross-Point-Chicago-Hotels.s50-n6132100-0.Travel-Guide-Filter-Hotels) - [Hotels near Baha'i House of Worship ](https://www.expedia.ca/Bahai-House-Of-Worship-Hotels.0-l6152644-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Botanic Garden ](https://www.expedia.ca/Chicago-Botanic-Garden-Hotels.0-l6064029-0.Travel-Guide-Filter-Hotels) - [Chicago Hotels ](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - 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