Find Vacation Rentals in Winnetka

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Winnetka
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Popular Winnetka Vacation Rentals

Find the perfect Winnetka vacation rental

House Winnetka
e.g. 5/27 - 6/3 (Sat - Sat)
-24%
$383
$293 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (7 ratings)
Winnetka, New Trier Township, Illinois, United States
Details
Vrbo
Details
Details
House Winnetka
e.g. 2/18 - 2/25 (Sat - Sat)
$166 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (6 ratings)
Winnetka, New Trier Township, Illinois, United States
Details
Vrbo
Details
Details
Condo Winnetka
e.g. 12/2 - 12/9 (Fri - Fri)
-29%
$223
$158 per night
Condo ∙ 14 guests ∙ 1 bedroom
Winnetka, New Trier Township, Illinois, United States
Details
Vrbo
Details
Details
Condo Winnetka
e.g. 12/2 - 12/9 (Fri - Fri)
-19%
$336
$271 per night
Condo ∙ 14 guests ∙ 2 bedrooms
4.8
"Excellent" (16 ratings)
Winnetka, New Trier Township, Illinois, United States
Details
Vrbo
Details
Details
Condo Winnetka
e.g. 12/2 - 12/9 (Fri - Fri)
-19%
$336
$271 per night
Condo ∙ 14 guests ∙ 2 bedrooms
5.0
"Excellent" (2 ratings)
Winnetka, New Trier Township, Illinois, United States
Details
Vrbo
Details
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Recommended Rentals With Pools

Condo Pool Winnetka
e.g. 12/2 - 12/9 (Fri - Fri)
-29%
$223
$158 per night
Condo ∙ 14 guests ∙ 1 bedroom
Winnetka, New Trier Township, Illinois, United States
Pool
Details
Vrbo
Details
Details
Condo Pool Winnetka
e.g. 5/13 - 5/20 (Sat - Sat)
-17%
$223
$185 per night
Condo ∙ 2 guests ∙ 1 bedroom
Winnetka, New Trier Township, Illinois, United States
Pool
Details
Vrbo
Details
Details
Condo Pool Winnetka
e.g. 12/2 - 12/9 (Fri - Fri)
-27%
$243
$178 per night
Condo ∙ 14 guests ∙ 1 bedroom
Winnetka, New Trier Township, Illinois, United States
Pool
Details
Vrbo
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Pet-Friendly Homes and Apartments

Apartment Pet-friendly Winnetka
$82 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Winnetka, New Trier Township, Illinois, United States
Pet-friendly
Details
Vrbo
Details
Details
Apartment Pet-friendly Winnetka
$109 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (1 rating)
Winnetka, New Trier Township, Illinois, United States
Pet-friendly
Details
Vrbo
Details
Details
Apartment Pet-friendly Winnetka
$83 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Winnetka, New Trier Township, Illinois, United States
Pet-friendly
Details
Vrbo
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Vacation Homes With Terraces

Apartment Balcony/Patio Winnetka
e.g. 5/27 - 6/3 (Sat - Sat)
$166 per night
Apartment ∙ 3 guests ∙ 1 bedroom
4.9
"Excellent" (37 ratings)
Winnetka, New Trier Township, Illinois, United States
Balcony/Patio
Details
Vrbo
Details
Details
Apartment Balcony/Patio Winnetka
e.g. 3/4 - 3/11 (Sat - Sat)
$258 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (21 ratings)
Winnetka, New Trier Township, Illinois, United States
Balcony/Patio
Details
Vrbo
Details
Details
House Balcony/Patio Winnetka
e.g. 12/3 - 12/10 (Sat - Sat)
-50%
$2,000
$1,000 per night
House ∙ 14 guests ∙ 4 bedrooms
5.0
"Excellent" (14 ratings)
Winnetka, New Trier Township, Illinois, United States
Balcony/Patio
Details
Vrbo
Details
Details
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Frequently Asked Questions

What is the price of vacation rentals in Winnetka?

In Winnetka, vacation rentals start at $74 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 15 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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