Search Far North Side 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
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Far North Side

Des Plaines Vacation Rental w/ Spacious Backyard!
Relax on the patio with a glass-top table and six comfortable chairs, surrounded by a patterned rug and a wooden deck.

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Stroll through a charming neighborhood with a mix of two-story and single-story homes, each with its own unique character.

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

3.0 star property
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Cozy Westmont Home: Walk to Metra Station!
Relax in a cozy Adirondack chair arrangement around a fire pit on this outdoor deck.

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!
2 Mi to Northwestern: Updated Home w/ Game Room!
Stunning two-story home with a charming front entrance and inviting porch.

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

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

3.0 star property
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Pet-friendly Bartlett Farmhouse w/ Deck!
Guests can enjoy a deck with a wooden fence, leading to a charming building with a window and door.

Pet-friendly Bartlett Farmhouse w/ Deck!

3.0 star property
Pet-friendly Bartlett Farmhouse w/ Deck!
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 Far North Side Hotel Reviews

Swissotel - Chicago

Swissotel - Chicago

10/10 Excellent
"The hotel was amazing get views and location the room was always clean but the pillows need to be better. The pillows sucked. "
Ted 3-night trip
Posted 7 hours ago
Swissotel - Chicago