Highwood Cottage Rentals & Holiday Homes

Frequently Asked Questions About Highwood Rental Cottages

What are the top rated Cottage Rentals in Highwood?

There are a lot of options in Highwood. If you plan on staying in the Highwood area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Highwood:

• Near Ravinia and Navy Base, charming 3-bedroom house in peaceful Highland Park
• Condo - Downtown Highland Park
• Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits
• 2 Bedroom apartment in Downtown Lake Bluff
• Safe & Secure Parkview-Sleep Sanctuary+Kitchen
• Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown
• Master qtr close to nature & easy urban facilities
• 2-Acre Highland Park Retreat with Heated Pool ~ 5*
• Serene Retreat Awaits You!
• 6 Kings Ping-Pong Gazebo!

How much does it cost to rent a cottage in Highwood?

The average cost for a cottage rental in Highwood is $592 per night. Vacation Cottage has a wide list of great cottages near Highwood that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Highwood that allow pets?

Yes, here are the top cottage rentals in Highwood that allow you to bring your pet:

• Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
• The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!
• Entire home, close to Ravinia Festival, Lake, Town, and Train to the city.
• Bright & Modern Home
• 2-Acre Highland Park Retreat with Heated Pool ~ 5*
• The Forester a Hyatt Place Hotel
• Safe & Secure Parkview-Sleep Sanctuary+Kitchen

See all pet-friendly vacation rentals in Highwood on Vacation Cottage

Do you have any rental cottages in Highwood that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Highwood to find one that works for you.

Are there quality cottages in Highwood that have indoor swimming pools?

As of 2025, the data from Vacation Cottage shows that there are Over 3 private swimming pools or cottages with indoor pools in the Highwood area along with other great amenities.

Do any cottages in Highwood have hot tubs?

About 3 cottages in Highwood boast of premium hot tubs. Some of the popular places to stay with hot tubs include:

• Highwood rentals with hot tub

Are there luxury cottages in Highwood?

Yes, there are luxury cottages in Highwood. Find more luxury, lakefront, winter, & last-minute cottage rentals near Highwood.