A vast wheat field under a cloudy sky.

Countryside Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Countryside vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,403 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is NT$4,435
NT$5,206 total
includes taxes & fees
Nov 22 - Nov 23
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (558 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is NT$5,609
NT$7,394 total
includes taxes & fees
Nov 23 - Nov 24
Level Chicago – Old Town
A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (83 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is NT$5,281
NT$8,229 total
includes taxes & fees
Dec 2 - Dec 3
Kasa Lake Shore Chicago
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

4. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (49 reviews)
"Clean room"
United States
Michael
The price is NT$5,432
NT$6,377 total
includes taxes & fees
Nov 9 - Nov 10
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Countryside Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Amazing stay, great amenities, breakfast was good had a lot of options. Area was nice and not to far from train services to get to Chicago."
Ray 4-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Countryside

Search for holiday rentals in Countryside on Expedia! You can easily find your home rentals, villas, holiday apartments in Countryside using one of the methods below:

  • View our selection of featured holiday rentals in Countryside
  • Use the map to find apartments and other holiday homes in the Countryside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Countryside while they last

Look no further and take a look at our great range of rental properties in Countryside!

Frequently asked questions

Can I find vacation rentals in Countryside?

Yes, we offer vacation rentals close to the most popular local attractions in Countryside, or you can select a secluded option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and shops in Countryside. Make sure you have time to check out the live music and zoo during your trip.

What can I see and do in Countryside?

Explore the area and family-friendly sights such as Childrens Museum of Oak Lawn, or get out into nature at a spot like Millennium Park. In the larger area, you’ll find popular places like Soldier Field and Navy Pier.

What are vacation rentals like in Countryside?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Countryside. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for families.