Photo by Tara Jabbari
Search Cottages in Highwood
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 12 Cottages in Highwood with updated reviews, rates, and availability.

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
10.0 out of 10, Exceptional, (1)

Des Plaines Vacation Rental w/ Spacious Backyard!
Des Plaines Vacation Rental w/ Spacious Backyard!

Romantic Lake Cottage for Two. With Patio and Firepit.
Romantic Lake Cottage for Two. With Patio and Firepit.
10.0 out of 10, Exceptional, (2)

Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town
Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town

Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!

Riverfront Libertyville Retreat w/ Outdoor Kitchen
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Lakefront Prospect Heights Home: Ice Fish On-site
Lakefront Prospect Heights Home: Ice Fish On-site

Private Coach house near Lincoln Square!
Private Coach house near Lincoln Square!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Highwood

Great 3 bedroom rental unit near Logan Square
Great 3 bedroom rental unit near Logan Square
9.6 out of 10, Exceptional, (24)

Charming Wrigleyville Home Close to the Cubs!
Charming Wrigleyville Home Close to the Cubs!
9.4 out of 10, Exceptional, (16)

Chic, Cozy home, by Blue Line Train Stop + Free parking
Chic, Cozy home, by Blue Line Train Stop + Free parking
9.4 out of 10, Exceptional, (44)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Highwood hotels
Recent reviews of Highwood hotels

Hyatt Regency O'Hare Chicago
5/5 Excellent
"Very nice. "
A verified traveler stayed at Hyatt Regency O'Hare Chicago
Posted 6 hours ago