Search Skokie Cottage Rentals

    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
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Skokie Cottages

Des Plaines Vacation Rental w/ Spacious Backyard!
Enjoy cooking in this well-lit kitchen with a gas stove, microwave, and stainless steel dishwasher.

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Fully equipped kitchen with refrigerator, stove, and oven, featuring a clean and organized layout.

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

3.0 star property
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
2 Mi to Northwestern: Updated Home w/ Game Room!
Enjoy cooking in this well-equipped kitchen with an oven, range hood, and granite countertop.

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!
Cozy Westmont Home: Walk to Metra Station!
Enjoy dining and socializing on the elevated deck, featuring a barbecue grill and comfortable seating.

Cozy Westmont Home: Walk to Metra Station!

3.0 star property
2.0 out of 10, (1)
"Very upset with the communication of this rental. I booked this rental for a weekend getaway with the family. I received an email a couple of days ahead of the booking reminding me of my trip and that I was all set. Then on check in day, I realized that I needed the check in information. I sent a message through the app to the renter. The response was "it may take a few days for the property to get back with you" so I called the number on the response. The operator then tried to look up my...
Cozy Westmont Home: Walk to Metra Station!
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and gas stove.

Home w/ Office + Yard: 25 Mi to Downtown Chicago!

3.0 star property
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
A charming single-story house with a gabled roof and a welcoming entrance.

8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

3.0 star property
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!
House (3 Bedrooms) | Front of property

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!
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Relax in a spacious room with high ceilings, large windows, and a cozy seating area.

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Glendale Heights Home With Office and Backyard!
Relax in this stylish living space with a sofa, coffee table, and kitchenette featuring a microwave and oven.

Glendale Heights Home With Office and Backyard!

3.0 star property
6.0 out of 10, (1)
Glendale Heights Home With Office and Backyard!
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Cozy living room with a leather sofa, ottoman, and dining area, featuring a fireplace and natural light.

Classic Oak Park Home, 11 Mi to Downtown Chicago!

3.0 star property
Classic Oak Park Home, 11 Mi to Downtown Chicago!
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, plus a stylish backsplash and wooden cabinets.

13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace

3.0 star property
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
Bike & Kayak: Lakefront Prospect Heights Home
House (4 Bedrooms) | Interior

Bike & Kayak: Lakefront Prospect Heights Home

3.0 star property
Bike & Kayak: Lakefront Prospect Heights Home
Private Coach house near Lincoln Square!
A minimalist space with a glass desk, round mirror, and potted plant.

Private Coach house near Lincoln Square!

Private Coach house near Lincoln Square!
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!
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!
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
Sign in
Sign up, it's free

Top Skokie Hotel Reviews

The Wade

The Wade

10/10 Excellent
"The view @ location was amazing!!!!"
Lori 2-night trip
Posted 5 hours ago
The Wade