Search Chicago 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

Cottages in Chicago

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Traditional home with a front porch, chimney, and yard.

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
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!
“The cottage” 2 bedrooms cozy and private home
Set amidst mature trees, this two-story house offers a serene residential setting with a well-manicured lawn and a charming chimney.

“The cottage” 2 bedrooms cozy and private home

9.4 out of 10, Exceptional, (8)
"We were at this location for 13 days while visiting family. It was just what we needed for our stay. Clean and functional, enough amenities for a long stay "
“The cottage” 2 bedrooms cozy and private home
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!
House (4 Bedrooms) | Interior

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

3.0 star property
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
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!
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Set amidst a serene yard with a large tree and a blue fence, this house features a gabled roof and a chimney.

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
Enjoy casual dining or social gatherings in this outdoor space with a table and chairs under a covered patio.

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Peaceful Warrenville Home: 1 Mi to Herrick Lake!
House (2 Bedrooms) | Interior

Peaceful Warrenville Home: 1 Mi to Herrick Lake!

3.0 star property
Peaceful Warrenville Home: 1 Mi to Herrick Lake!
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Stunning two-story home with a charming garden and bay window.

Classic Oak Park Home, 11 Mi to Downtown Chicago!

3.0 star property
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Country Club Hills Home: Walk to Rec Center!
Set amidst mature trees in a quiet suburban neighborhood, this single-story house offers a serene retreat.

Country Club Hills Home: Walk to Rec Center!

3.0 star property
Country Club Hills Home: Walk to Rec Center!
Glendale Heights Home With Office and Backyard!
Cozy home with a front entrance, porch, and garage, set amidst a grassy yard.

Glendale Heights Home With Office and Backyard!

3.0 star property
6.0 out of 10, (1)
Glendale Heights Home With Office and Backyard!
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!
Spacious Family Glenwood Estates Home w/ Hot Tub!
House (4 Bedrooms) | Interior

Spacious Family Glenwood Estates Home w/ Hot Tub!

3.0 star property
Spacious Family Glenwood Estates Home w/ Hot Tub!
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
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
Homes in this neighborhood feature a mix of brick and stucco facades, set amidst well-maintained lawns and sidewalks.

13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace

3.0 star property
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
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!
Exterior

Elegant Mount Prospect Home w/ Fire Pit!

3.0 star property
Elegant Mount Prospect Home w/ Fire Pit!
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 Chicago Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"We came for a wedding and had a blast! This hotel is beautiful and we love it!"
Djenita 2-night trip
Posted 5 hours ago
InterContinental Chicago Magnificent Mile by IHG

Frequently asked questions

Why book your cottage in Chicago with Expedia?
Expedia has some wonderful cottages in Chicago, so start packing for an unforgettable vacation on nature's doorstep. If you need to stick to a budget, click on how much you'd like to spend and your preferred property star rating. Or, make the most of our filters to search for cottages with free WiFi or a pool. We'll help you find the perfect fit whatever your style of travel or plans.
How can I find cheap cottages in Chicago?
An excellent way to compare cheap cottages in Chicago is with Expedia's user-friendly filter tool. Refine your search results by amenities, budget and star rating to take advantage of awesome bargains with only a few clicks.
What is there to do in Chicago near my cottage?
Chicago has enough activities and experiences to keep you going for weeks, beginning with Anna and Frederick Douglass Park. Grant Park, Marquette Park and Midway Plaisance are other popular attractions. If you're hanging around a while, Ernest Hemingway Museum and House and Bridgehouse and Chicago River Museum are great additions to your itinerary.