Winnetka Summer Rentals, Cottages & Cabins

Book a Place to Stay in Winnetka for Your Summer Getaway

About Winnetka Summer Rental on SunSkiResorts

SunSki's selection of summer rentals in Winnetka promises the ideal setting for your next seasonal escape. We offer a diverse array of properties boasting enticing features such as private pools, indoor/outdoor swimming facilities, hot tubs, WiFi, beachfront access, and more. Whether you're journeying with family, friends, or a larger group, we have a rental perfectly tailored to your requirements.

Immerse yourself in the epitome of summer leisure in Winnetka with SunSki. Our summer rental accommodations are meticulously curated to ensure utmost comfort and relaxation. From chic condos and opulent resorts to charming villas, quaint bungalows, cozy cabins, RVs, and cottages, we present a spectrum of options to match your vacation vision. Discover your idyllic summer retreat with SunSki.

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Frequently Asked Questions About Winnetka Luxury Rentals

There are a lot of options in Winnetka. If you plan on staying in the Winnetka area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Winnetka:

In 2025, SunSki offers 28 summer rentals in or around Winnetka. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Winnetka is $343. Check the full list of summer accommodations in Winnetka.
There are 28 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with SunSkiResorts.

Yes, here are some popular summer holiday rentals in Winnetka that have a private or indoor pool:

Check all holiday rentals with a pool in Winnetka on SunSkiResorts.

Yes, We have 28 summer rental homes in Winnetka and types of place to stay in Winnetka include:

  • Vacation Homes: 28 available for rent
  • Villas: 28 Rentals available for rent
  • Holiday Apartments: 28 Rentals available for rent
  • Hotels with Suites: 28 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Winnetka. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Winnetka.