A vast wheat field under a cloudy sky.

Countryside Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Countryside vacation rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,306 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is ￥23,775
￥32,495 total
includes taxes & fees
Sep 8 - Sep 9
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (26 reviews)
"Great location and super clean!"
United States
Erica
The price is ￥25,525
￥39,633 total
includes taxes & fees
Sep 9 - Sep 10
Kasa Lake Shore Chicago
Full-size fridge, microwave, oven, stovetop

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (522 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is ￥44,696
￥56,323 total
includes taxes & fees
Sep 8 - Sep 9
Level Chicago – Old Town
Living area

4. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.2 out of 10, Very Good, (54 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is ￥23,205
￥27,240 total
includes taxes & fees
Sep 8 - Sep 9
Wrigleyville Suites
Apartment, Private Bathroom | Lounge

5. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is ￥35,549
￥58,049 total
includes taxes & fees
Sep 21 - Sep 22
At Home in Oak Park
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

6. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is ￥37,256
￥60,001 total
includes taxes & fees
Sep 14 - Sep 15
Historic Oak Park Home
House (3 Bedrooms) | Interior

7. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is ￥37,815
￥74,197 total
includes taxes & fees
Sep 8 - Sep 9
Classic Forest Park Foursquare < 1 Mi to Blue Line
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

8. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is ￥37,573
￥60,365 total
includes taxes & fees
Sep 30 - Oct 1
Historic Oak Park Residence
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

9. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ￥39,110
￥62,124 total
includes taxes & fees
Sep 12 - Sep 13
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.
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Top Countryside Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Loved our room! Beautiful view"
Mary Carmen 1-night trip
Posted less than an hour ago
Hilton Chicago

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:

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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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental near Countryside is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.