102+ Vacation Rentals & Holiday Homes in Highwood |
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Highwood Accommodations - Hotels & Rentals

About Highwood Vacation Rentals

Discover More than 102 Incredible Getaway Rentals Available in Highwood. 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 Highwood.

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 Highwood, 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 Highwood. The Average Size of Places to Stay Near Highwood is 579.8 ft², with Prices Averaging US $328 per Night.

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

Type Count
Vacation Homes 36
Holiday Apartments 17
Cottages 3
Villas 3

Use these Quick Filters to Find a Vacation Rental in Highwood

★ 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 Highwood with Online Reservations.

Weather in Highwood, IL

View the weather forecast for Highwood before booking your Highwood 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 HighwoodGuest Reviews Local Attractions

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


Naval Base Great Lakes
Six Flags Great America
Northwestern University
Allstate Arena
Loyola University Chicago
Schaumburg Convention Center
Rosemont Theatre
Woodfield Mall
Donald E. Stephens Convention Center
Gurnee Mills
Rivers Casino
Aragon Ballroom
Legoland Discovery Center
Riviera Theatre
Schaumburg Medieval Times
Illinois Beach State Park
Fashion Outlets of Chicago
Genesee Theater
Baha'i House of Worship
Parkway Bank Park Entertainment District

Frequently Asked Questions About Highwood?

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

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

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

Searching for a family-friendly getaway in Highwood? 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 Highwood?

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 102 in the Highwood 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 Highwood.


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