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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

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

Lakehouse Getaway
Property grounds

Lakehouse Getaway

Lakehouse Getaway
Little Fox Cottage - A Cozy Riverview Getaway
Exterior

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 AED 441
AED 715 total
includes taxes & fees
23 Jan - 24 Jan
Little Fox Cottage - A Cozy Riverview Getaway
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Living area

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

3.0 star property
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Cozy 3 bedroom river cottage w/ indoor fireplace
Outdoor dining

Cozy 3 bedroom river cottage w/ indoor fireplace

9.8 out of 10, Exceptional, (15)
"Overall, the stay was great. Slight issue in check in with the door handle being upside down, but everything else was great"
Cozy 3 bedroom river cottage w/ indoor fireplace
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Living area

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!
Exterior

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!
Living area

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.
Private kitchen

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.
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Living area

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Lakefront Prospect Heights Home: Ice Fish On-site
Living area

Lakefront Prospect Heights Home: Ice Fish On-site

3.0 star property
Lakefront Prospect Heights Home: Ice Fish On-site
Fox River Grove Home: Pets Welcome!
Exterior

Fox River Grove Home: Pets Welcome!

3.0 star property
Fox River Grove Home: Pets Welcome!
Charming Illinois Retreat w/ Hot Tub, Deck & Grill
Living area

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!
Outdoor dining

Elegant Mount Prospect Home w/ Fire Pit!

3.0 star property
Elegant Mount Prospect Home w/ Fire Pit!
Safe Spacious Mansion Indowntown
Front of property

Safe Spacious Mansion Indowntown

4.0 star property
Safe Spacious Mansion Indowntown
Day Trip to Chicago: Hoffman Estates Gem!
Interior

Day Trip to Chicago: Hoffman Estates Gem!

3.0 star property
Day Trip to Chicago: Hoffman Estates Gem!
Prime Location Old Town Chicago Townhome!
Living area

Prime Location Old Town Chicago Townhome!

3.0 star property
Prime Location Old Town Chicago Townhome!
Private Coach house near Lincoln Square!
Room

Private Coach house near Lincoln Square!

Private Coach house near Lincoln Square!
Chicago Home w/ Hot Tub < 2 Mi to Wrigley Field
Lobby

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

3.0 star property
Chicago Home w/ Hot Tub < 2 Mi to Wrigley Field
Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town
Welcome to our Storybook Cottage 🏡, gushing w/ cozy-warm-spacious glitz+comfort💞

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!
Living area

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

3.0 star property
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
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
Sign in
Sign up, it's free

Other property types in Highland Park

Level Chicago – Old Town
Outdoor pool

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (285)
"The lady in the front was amazing and very helpful."
The price is AED 611
AED 799 total
includes taxes & fees
26 Jan - 27 Jan
Level Chicago – Old Town
Walking distance to restaurants, shops and Lake Michigan,
Large kitchen with open floor plan, hardwood floor throughout.

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (175)
"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!
Living area

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (70)
"convienent location "
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.