Photo by Meghan hernandez

Search Cottages in Highland Park

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 21 Cottages in Highland Park with updated reviews, rates, and availability.

Cozy 3 bedroom river cottage w/ indoor fireplace

9.8 out of 10, Exceptional, (14)
"Great stay with a convenient location. The extra pack-n-play was a nice touch. Definitely recommend this property to anyone."
Cozy 3 bedroom river cottage w/ indoor fireplace

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard

3.0 star property
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard

Little Fox Cottage - A Cozy Riverview Getaway

10.0 out of 10, Exceptional, (14)
"I was very grateful to get away for a few days of quiet & calm in this lovely cottage. It feels incredibly homey and a place to just relax. The details are perfect and the fireplace on the patio is an added bonus. "
The price is SAR 507
SAR 803 total
includes taxes & fees
6 Jan - 7 January 2025
Little Fox Cottage - A Cozy Riverview Getaway

Classic Oak Park Home, 11 Mi to Downtown Chicago!

3.0 star property
Classic Oak Park Home, 11 Mi to Downtown Chicago!

Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
"So cozy. Feels like staying in a guest house with the whole place to yourself! "
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!

Romantic Lake Cottage for Two. With Patio and Firepit.

10.0 out of 10, Exceptional, (2)
"Perfect location to relax and visit with family in the area."
Romantic Lake Cottage for Two. With Patio and Firepit.

Eclectic Grayslake Home w/ Private Yard & Fire Pit

3.0 star property
2.0 out of 10, (1)
"DO NOT book this property. We made our reservation before leaving on our driving trip, and everything was good. I contacted them a couple of days before our arrival and was given instructions for accessing the property. Upon arrival, we were unable to enter the property. The owner spoke with us via Ring camera, and said we'd canceled our stay. I told the owner we hadn't canceled, so he got the 3rd party management firm he uses on a conference call. That firm claimed our card was declined...
Eclectic Grayslake Home w/ Private Yard & Fire Pit

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Lakefront Home w/ Deck & Grill in Prospect Heights

3.0 star property
Lakefront Home w/ Deck & Grill in Prospect Heights

Fox River Grove Home: Pets Welcome!

3.0 star property
Fox River Grove Home: Pets Welcome!

Charming Illinois Retreat w/ Hot Tub, Deck & Grill

3.0 star property
Charming Illinois Retreat w/ Hot Tub, Deck & Grill

Elegant Mount Prospect Home w/ Fire Pit!

3.0 star property
Elegant Mount Prospect Home w/ Fire Pit!

The Winchester - Custom Home w Amazing Outdoors

3.5 star property
The Winchester - Custom Home w Amazing Outdoors

Safe Spacious Mansion Indowntown

4.0 star property
Safe Spacious Mansion Indowntown

Day Trip to Chicago: Hoffman Estates Gem!

3.0 star property
Day Trip to Chicago: Hoffman Estates Gem!

Lakehouse Getaway

Lakehouse Getaway

Prime Location Old Town Chicago Townhome!

3.0 star property
Prime Location Old Town Chicago Townhome!

Private Coach house near Lincoln Square!

Private Coach house near Lincoln Square!

Chicago Home w/ Hot Tub < 2 Mi to Wrigley Field

3.0 star property
Chicago Home w/ Hot Tub < 2 Mi to Wrigley Field
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.
Don't see what you're looking for?
See all available properties in Highland Park
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Highland Park

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (277)
"I loved the amenities available to us - garage parking, washer/dryer in unit, full kitchen and fully furnished. Staff were polite and helpful. Great location"
The price is SAR 664
SAR 854 total
includes taxes & fees
3 Jan - 4 January 2025
Level Chicago – Old Town

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (174)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (67)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +parking!
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.

Frequently asked questions

Why book your cottage in Highland Park with Expedia?
Booking a cottage in Highland Park is as easy as clicking on your travel dates and picking an ideal place for a vacation in nature. From ritzy retreats to low-cost properties and cottages that offer amenities like a kitchenette, Expedia has something for all styles. As for epic deals? We’ve got your back!
How can I find cheap cottages in Highland Park?
With Expedia’s helpful filter tool, comparing cheap cottages in Highland Park couldn’t be easier. To view properties that’ll make your hip pocket happy, narrow down your search by budget, star rating and amenities.