46+ Vacation Rentals & Holiday Homes in Winnetka |
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Winnetka Accommodations - Hotels & Rentals

About Winnetka Vacation Rentals

Discover More than 46 Incredible Getaway Rentals Available in Winnetka. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Winnetka.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Winnetka, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Winnetka. The Average Size of Places to Stay Near Winnetka is 689.41 ft², with Prices Averaging US $308 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Winnetka. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Winnetka

Type Count
Vacation Homes 36
Holiday Apartments 3
Villas 2

Use these Quick Filters to Find a Vacation Rental in Winnetka

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Winnetka with Online Reservations.

Weather in Winnetka, CA

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

Activities WinnetkaGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World WinnetkaGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Universal Studios Hollywood
Venice Beach
Santa Monica Pier
Six Flags Magic Mountain
Hollywood Walk of Fame
Santa Monica Beach
Melrose Avenue
University of California Los Angeles
The Grove
Venice Beach Boardwalk
Warner Brothers Studio
Universal CityWalk
Rodeo Drive
Sunset Strip
Dolby Theater
Griffith Observatory
La Brea Tar Pits
Hollywood Sign
The Wizarding World of Harry PotterTM
Los Angeles Zoo

Frequently Asked Questions About Winnetka?

What are the top hotels, lake houses & vacation rentals in Winnetka?

We provide an array of great vacation destinations in Winnetka. If you are looking to stay in or around the Winnetka area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Winnetka:

How many Hotels & Vacation Rentals have private pools in Winnetka?

We have 1 Hotels & Vacation Rentals featuring a private pool in and near Winnetka. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Winnetka is best for families?

Searching for a family-friendly getaway in Winnetka? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Winnetka?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 46 in the Winnetka area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Winnetka.


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