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

Winnetka Luxury Rental Homes and Villas

Find Luxury Places to Stay Near Winnetka

About Winnetka Luxury Rental on PickleTrip

PickleTrip™ luxury rentals offer a wide range of amenities, including pickleball courts or nearby facilities, private pools, hot tubs, saunas, game rooms, home theaters, fully equipped kitchens, and spacious living areas. These properties are perfect for those looking for a luxurious and comfortable getaway in Winnetka. Whether you are looking for sporty getaway, a romantic retreat, a family vacation, or a gathering with friends, our luxury rentals have everything you need to make your stay unforgettable.

With PickleTrip™, you can choose from a wide range of luxury rental properties, including villas, penthouses, beachfront resorts, and more. Each rental is designed to provide you with the ultimate comfort and luxury, while you enjoy your stay in Winnetka. Browse our selection of luxury rentals today and book your dream pickleball vacation with PickleTrip™.

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 Luxury Rentals in Winnetka:

We have many pet-friendly luxury rentals in the Winnetka. The top pet-friendly rentals in Winnetka are:

See all pet-friendly rentals in Winnetka on PickleTrip

Yes, there are more than 37 luxury resorts & villas rentals in Winnetka that have indoor/outdoor and private swimming pools. Check out our filter option and find your best places to stay near Winnetka.
Most of the luxury holiday rentals have an internet facility on PickleTrip. These are some popular places to stay in Winnetka that have internet access:

There are more than 37 luxury rentals with hot tubs available for rent in Winnetka.