93+ Vacation Rentals & Holiday Homes in Westchester |
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Westchester Accommodations - Hotels & Rentals

About Westchester Vacation Rentals

Discover More than 93 Incredible Getaway Rentals Available in Westchester. 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 Westchester.

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 Westchester, 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 Westchester. The Average Size of Places to Stay Near Westchester is 594.7 ft², with Prices Averaging US $460 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Westchester. 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 Westchester

Type Count
Vacation Homes 49
Holiday Apartments 11
Villas 1

Use these Quick Filters to Find a Vacation Rental in Westchester

★ 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 Westchester with Online Reservations.

Weather in Westchester, IL

View the weather forecast for Westchester before booking your Westchester 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 WestchesterGuest Reviews Local Attractions

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


Fresh Meadow Golf Club
Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
United Center
Grant Park
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
University of Chicago
Brookfield Zoo
Northwestern University
John Hancock Center

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Fresh Meadow Golf Club 93 Properties

Frequently Asked Questions About Westchester?

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

We provide an array of great vacation destinations in Westchester. If you are looking to stay in or around the Westchester 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 Westchester:

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

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 93 in the Westchester 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 Westchester.


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