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Search Cottages in Highland Park

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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 22 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, (15)
"The perfect place for a quiet winter weekend getaway. Relax and enjoy!"
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
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
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
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!
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!
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.
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!
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
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
Fox River Grove Home: Pets Welcome!
Exterior

Fox River Grove Home: Pets Welcome!

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

Private Coach house near Lincoln Square!

Private Coach house near Lincoln Square!
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!
Outdoor dining

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
Room

The Winchester - Custom Home w Amazing Outdoors

3.5 star property
The Winchester - Custom Home w Amazing Outdoors
Safe Spacious Mansion Indowntown
Front of property

Safe Spacious Mansion Indowntown

4.0 star property
Safe Spacious Mansion Indowntown
2 Mi to Northwestern: Updated Home w/ Game Room!
Living area

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

3.0 star property
2 Mi to Northwestern: Updated Home w/ Game Room!
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.
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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, (288)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is SAR 540
SAR 718 total
includes taxes & fees
27 Feb - 28 Feb
Level Chicago – Old Town
Great 3 bedroom rental unit near Logan Square
Interior

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (23)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square
Wrigleyville Suites
Terrace/patio

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is SAR 301
SAR 541 total
includes taxes & fees
24 Feb - 25 Feb
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.

Frequently asked questions

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