151+ Vacation Rentals & Holiday Homes in Chester Highlands |
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Chester Highlands Accommodations - Hotels & Rentals

About Chester Highlands Vacation Rentals

Discover More than 151 Incredible Getaway Rentals Available in Chester Highlands. 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 Chester Highlands.

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 Chester Highlands, 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 Chester Highlands. The Average Size of Places to Stay Near Chester Highlands is 728.49 ft², with Prices Averaging US $302 per Night.

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

Type Count
Vacation Homes 72
Holiday Apartments 63
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Chester Highlands

★ 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 Chester Highlands with Online Reservations.

Weather in Chester Highlands, IL

View the weather forecast for Chester Highlands before booking your Chester Highlands 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 Chester HighlandsGuest Reviews Local Attractions

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


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
John Hancock Center
Lincoln Park Zoo
Water Tower Place

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Gresham 105 Properties
Auburn Gresham 96 Properties

Frequently Asked Questions About Chester Highlands?

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

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

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

Searching for a family-friendly getaway in Chester Highlands? 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 Chester Highlands?

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 151 in the Chester Highlands 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 Chester Highlands.

Nearby Neighborhood (1) 
Neighborhood Property Count
Chatham Vacation Rentals in Chicago, Illinois 192

People Also Ask

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