Photo by Meghan hernandez

Search Cottages in Highland Park

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 24 Cottages in Highland Park with updated reviews, rates, and availability.

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
TV, fireplace, books

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

3.0 star property
10.0 out of 10, Exceptional, (1)
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Cozy 3 bedroom river cottage w/ indoor fireplace
Smart TV, fireplace

Cozy 3 bedroom river cottage w/ indoor fireplace

9.8 out of 10, Exceptional, (16)
"Lovely, updated, perfect place for a girls reunion weekend! We enjoyed our stay very much!"
Cozy 3 bedroom river cottage w/ indoor fireplace
Lakehouse Getaway
Miscellaneous

Lakehouse Getaway

Lakehouse Getaway
2 Mi to Northwestern: Updated Home w/ Game Room!
Interior

2 Mi to Northwestern: Updated Home w/ Game Room!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This recently remodeled home was perfect for our family trip. It was immaculate, comfortable, spacious and well appointed. "
2 Mi to Northwestern: Updated Home w/ Game Room!
Amazing summer lake escape in our waterfront cottage!!!
Exterior

Amazing summer lake escape in our waterfront cottage!!!

9.4 out of 10, Exceptional, (35)
"A perfect place to get away and not have to worry about crowds of people! The boats, the lake and pier access were the best! The owners were so kind to leave my grandkids a huge strong blowup which we tied to the pier and the kids spent hours jumping off into the water! All three of my grandkids caught their first fish right off the pier! We all kayaked for the first time! Highly recommend!"
Amazing summer lake escape in our waterfront cottage!!!
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Interior

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

3.0 star property
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Little Fox Cottage - A Cozy Riverview Getaway
Property grounds

Little Fox Cottage - A Cozy Riverview Getaway

10.0 out of 10, Exceptional, (15)
"The perfect place for a quiet winter weekend getaway. Relax and enjoy!"
The price is AED 569
AED 876 total
includes taxes & fees
14 May - 15 May
Little Fox Cottage - A Cozy Riverview Getaway
Des Plaines Vacation Rental w/ Spacious Backyard!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Fireplace

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!
Romantic Lake Cottage for Two. With Patio and Firepit.
Beach

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.
Fox River Grove Home: Pets Welcome!
Interior

Fox River Grove Home: Pets Welcome!

3.0 star property
Fox River Grove Home: Pets Welcome!
Private Coach house near Lincoln Square!
Interior

Private Coach house near Lincoln Square!

Private Coach house near Lincoln Square!
Lakefront Prospect Heights Home: Ice Fish On-site
Interior

Lakefront Prospect Heights Home: Ice Fish On-site

3.0 star property
Lakefront Prospect Heights Home: Ice Fish On-site
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!
Elegant Mount Prospect Home w/ Fire Pit!
Interior

Elegant Mount Prospect Home w/ Fire Pit!

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

Safe Spacious Mansion Indowntown

4.0 star property
Safe Spacious Mansion Indowntown
The Winchester - Custom Home w Amazing Outdoors
3 bedrooms, iron/ironing board, free WiFi

The Winchester - Custom Home w Amazing Outdoors

3.5 star property
The Winchester - Custom Home w Amazing Outdoors
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
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (311)
"It was really nice overall! Would recommend "
The price is AED 806
AED 1,028 total
includes taxes & fees
12 May - 13 May
Level Chicago – Old Town
The Gem Museum Suites
Reception

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (61)
"This hotel was outstanding in all respects. "
The price is AED 705
AED 807 total
includes taxes & fees
12 May - 13 May
The Gem Museum Suites
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
8.4 out of 10, Very Good, (6)
The price is AED 476
AED 742 total
includes taxes & fees
12 May - 13 May
Wrigleyville Suites
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.