Find Vacation Rentals in Winnetka


Recommended Rentals With Pools

House Pool Winnetka
House ∙ 7 guests ∙ 4 bedrooms
Winnetka, New Trier Township, Illinois, United States
from $335
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Best vacation rentals with a balcony

House Balcony Winnetka
House ∙ 16 guests ∙ 4 bedrooms
Winnetka, New Trier Township, Illinois, United States
from $733
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Finding the perfect vacation home has never been easier. searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, and more. When you use to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Winnetka

Looking for the perfect vacation rental for your Winnetka getaway?’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Winnetka offers 75 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 55 properties with high-speed WiFi Internet, 26 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget. For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $25 a month. Save hundreds with affordable vacation rentals on and, in many cases, book directly online so you’re all set to go. Winnetka has 75 gorgeous homes with 24 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Search properties from 7 vacation rental sites in Winnetka where the top providers in that area are HRS Holidays, HomeAway, and There are 24 HRS Holidays rentals, 15 HomeAway short term rentals and 14 vacation rentals.

Popular Day Trips Near Winnetka