1. USA
  2. Illinois
  3. Chicago
  4. Winnetka
  5. Summer Rental

Winnetka Summer Rentals, Cottages & Cabins

Book a Place to Stay in Winnetka for Your Summer Getaway

About Winnetka Summer Rental on Rent By Owner

With 27 summer rentals in or near Winnetka, choosing a suitable rental home for your upcoming summer getaway on Rent By Owner is easy. Whether you are traveling with family, friends, or in a group to Winnetka or areas nearby, RBO has plenty of summer accommodations to choose from, many with top amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxury bedrooms, bathtubs, and pet-allowed environments.

Looking for a relaxing place to stay in Winnetka for a summer vacation you do not want to forget easily? Rent By Owner summer rental homes are available to provide you with the maximum comfort you deserve. Whether you're needing a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Winnetka, RBO has got you covered for your next summer holiday.

Show more
Show less

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, RBO offers 27 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 $363. Check the full list of summer accommodations in Winnetka.
There are 27 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Rent By Owner.

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 Rent By Owner.