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
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Countryside vacation rentals

Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (416 reviews)
"Property was clean, welcoming, pet friendly "
United States
Heather
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,066 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is ￥16,793
￥24,208 total
includes taxes & fees
Feb 1 - Feb 2
Sentral Michigan Avenue
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (29 reviews)
"Nice place "
United States
Barry
The price is ￥22,286
￥26,161 total
includes taxes & fees
Jan 31 - Feb 1
Wrigleyville Suites
Apartment, Private Bathroom | Lounge

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
United States
Kathryn
At Home in Oak Park
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Wanted a house in oak park and this was such a pleasant, comfortable and convenient place. Really comfortable beds too. Even a lovely piano. "
United States
judith
The price is ￥23,685
￥44,120 total
includes taxes & fees
Feb 1 - Feb 2
Historic Oak Park Home
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
Harvey
4.2 out of 10, (71 reviews)
"Under renovations so some rooms have missing appliances, even through an app they require a deposit. Utter wise nice room and workers"
United States
Destin
The price is ￥12,955
￥14,635 total
includes taxes & fees
Jan 31 - Feb 1
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Absolutely awesome "
United States
Erik
The price is ￥23,685
￥44,120 total
includes taxes & fees
Feb 1 - Feb 2
Historic Oak Park Residence
Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ￥18,309
￥37,966 total
includes taxes & fees
Feb 1 - Feb 2
The Oak Park Loft
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 Wade

The Wade

10/10 Excellent
"Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. "
Norah 4-night trip
Posted 21 hours ago
The Wade

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 are some of the best vacation rentals that Countryside has to offer?

A Home Away From Home!: This vacation home rental near Countryside offers a fireplace, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

What can I see and do in Countryside?

Explore the area and family-friendly sights such as Parkway Bank Park Entertainment District, or get out into nature at a spot like Grant Park. In the larger area, you’ll find popular places like Michigan Avenue and Wrigley Field.

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.