Photo by Steve Luzzo

Search Cottages in Far Southwest Side

    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
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Far Southwest Side

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!
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!
4 Mi to Lake Michigan: East Chicago Home w/ Grill
Enjoy cooking in this well-equipped kitchen with a stainless steel range, microwave, and sink.

4 Mi to Lake Michigan: East Chicago Home w/ Grill

3.0 star property
4 Mi to Lake Michigan: East Chicago Home w/ Grill
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!
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!
3 Mi to Hard Rock Casino: Charming Home in Gary!
Interior

3 Mi to Hard Rock Casino: Charming Home in Gary!

3.0 star property
3 Mi to Hard Rock Casino: Charming Home in Gary!
Gary Vacation Rental ~ 5 Mi to Lake Michigan!
Stunning two-story house with a central entrance, flanked by windows and a small chimney.

Gary Vacation Rental ~ 5 Mi to Lake Michigan!

3.0 star property
Gary Vacation Rental ~ 5 Mi to Lake Michigan!
Spacious Family Glenwood Estates Home w/ Hot Tub!
Interior

Spacious Family Glenwood Estates Home w/ Hot Tub!

3.0 star property
Spacious Family Glenwood Estates Home w/ Hot Tub!
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
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