34+ Private Villas and Holiday Rentals in Winnetka |
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Winnetka Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Winnetka

Discover more than 34 vacation rentals available in Winnetka. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winnetka.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winnetka, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winnetka. On average, places to stay near Winnetka offer 735.3 ft², with nightly prices averaging GB £252.

With Casai, finding and comparing holiday rentals in Winnetka is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Winnetka

Type Count
Vacation Homes 20
Holiday Apartments 2
Villas 1

Use these Quick Filters to Find a Holiday Rental in Winnetka

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winnetka.

Weather in Winnetka, IL

View the weather forecast for Winnetka before booking your Winnetka Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Winnetka, IL

Casai offers a large selection of top attractions around Winnetka . Research things to do on your vacation before you visit Winnetka.


Chocolate Box
Maple Street Beach
Elder Lane Beach
Home Alone House
Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
Naval Base Great Lakes
United Center
Grant Park
John G. Shedd Aquarium
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
Brookfield Zoo

Other Places to Stay in Winnetka, IL


Chocolate Box 273 Properties
Home Alone House 255 Properties
Maple Street Beach 251 Properties
Northfield 59 Properties
Elder Lane Beach 48 Properties
New Trier 30 Properties

Frequently Asked Questions About Winnetka?

What are the top holiday rentals in Winnetka?

With numerous options available in Winnetka, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winnetka:

Which holiday homes in Winnetka are best for families?

If you're searching for a family-friendly holiday home in Winnetka, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winnetka:

How many Casai.uk holiday rentals are available in Winnetka?

As of 2025, Casai boasts over 34 properties listed in the Winnetka area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winnetka.


People Also Ask

There are 34 Winnetka, IL Holiday Rentals

Recently Booked Holiday Rentals in Winnetka