Find Vacation Rentals in Winnetka

We have 61 properties to choose from
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Popular Winnetka Vacation Rentals

Find the perfect Winnetka vacation rental

House Winnetka
from $494 per night
House ∙ 7 guests ∙ 4 bedrooms

177 m² House

4.9
Outstanding(18 ratings)
Winnetka, New Trier Township, Illinois, United States
Details
House Winnetka
from $270 per night
6 guests ∙ 2 bedrooms

House

4.9
Outstanding(14 ratings)
Winnetka, New Trier Township, Illinois, United States
Details
House Winnetka
from $223 per night
6 guests ∙ 3 bedrooms

House

Winnetka, New Trier Township, Illinois, United States
Details
Apartment Winnetka
from $139 per night
Apartment ∙ 2 guests ∙ 1 bedroom

47 m² Apartment

Winnetka, New Trier Township, Illinois, United States
Details
Apartment Winnetka
from $110 per night
Apartment ∙ 2 guests ∙ 1 bedroom

47 m² Apartment

5.0
Outstanding(1 rating)
Winnetka, New Trier Township, Illinois, United States
Details
Apartment Winnetka
from $131 per night
Apartment ∙ 2 guests ∙ 1 bedroom

56 m² Apartment

Winnetka, New Trier Township, Illinois, United States
Details
Apartment Winnetka
from $152 per night
Apartment ∙ 2 guests ∙ 1 bedroom

56 m² Apartment

Winnetka, New Trier Township, Illinois, United States
Details
Apartment Winnetka
from $168 per night
Apartment ∙ 2 guests ∙ 1 bedroom

47 m² Apartment

Winnetka, New Trier Township, Illinois, United States
Details
Apartment Winnetka
from $121 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

65 m² Apartment

Winnetka, New Trier Township, Illinois, United States
Details
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Recommended Rentals With Pools

Studio flat  Winnetka
from $165 per night
2 guests ∙ 1 bedroom

Studio flat

Winnetka, New Trier Township, Illinois, United States
Pool
Details
Condo  Winnetka
from $203 per night
2 guests ∙ 1 bedroom

Condo

Winnetka, New Trier Township, Illinois, United States
Pool
Details
House  Winnetka
from $1,132 per night
House ∙ 14 guests ∙ 5 bedrooms

325 m² House

5.0
Outstanding(21 ratings)
Winnetka, New Trier Township, Illinois, United States
Pool
Details
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Pet-Friendly Homes and Apartments

House  Winnetka
from $347 per night
House ∙ 12 guests ∙ 3 bedrooms

172 m² House

Winnetka, New Trier Township, Illinois, United States
Pet-friendly
Details
House  Winnetka
from $1,152 per night
House ∙ 7 guests ∙ 4 bedrooms

557 m² House

5.0
Outstanding(7 ratings)
Winnetka, New Trier Township, Illinois, United States
Pet-friendly
Details
Apartment  Winnetka
from $229 per night
5 guests ∙ 2 bedrooms

Apartment

5.0
Outstanding(2 ratings)
Winnetka, New Trier Township, Illinois, United States
Pet-friendly
Details
Show more

Frequently Asked Questions

What is the price of vacation rentals in Winnetka?

In Winnetka, vacation rentals start at $109 per night.

Is it possible to compare multiple vacation rentals in Winnetka?

Our large collection of vacation homes makes it easy to filter and compare 61 offers in Winnetka.

Finding the perfect vacation home has never been easier. Tripping.com 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, Booking.com and more. When you use Tripping.com 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? Tripping.com’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 Tripping.com 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 Tripping.com. Search properties from 7 vacation rental sites in Winnetka where the top providers in that area are HRS Holidays, HomeAway, and Booking.com. There are 24 HRS Holidays rentals, 15 HomeAway short term rentals and 14 Booking.com vacation rentals.

Popular Day Trips Near Winnetka

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