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Countryside Holiday Rentals

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Our top choices for Countryside holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1026)
"My favorite place to stay hands-down"
United States
Michele
The price is AU$250
includes taxes & fees
6 Jan - 7 Jan 2026
Sentral Michigan Avenue

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (5)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is AU$230
includes taxes & fees
7 Jan - 8 Jan 2026
Chicago luxury home suites

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AU$254
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is AU$249
includes taxes & fees
6 Jan - 7 Jan 2026
Gold Coast Living: Modern Studio Unit

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is AU$254
includes taxes & fees
6 Jan - 7 Jan 2026
West Loop Living – Bright 1BR

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.8 out of 10, Exceptional, (16)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is AU$287
includes taxes & fees
1 Jan - 2 Jan 2026
Twice as Nice: Chic 2BR Stay with Style & Space

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is AU$254
includes taxes & fees
5 Jan - 6 Jan 2026
Sun-Drenched 1BR Apartment

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is AU$254
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is AU$254
includes taxes & fees
7 Jan - 8 Jan 2026
The One: A 1BR Stay That Feels Like Home

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is AU$473
includes taxes & fees
5 Jan - 6 Jan 2026
River North Rooftop With In and Out Parking 3

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (406)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is AU$254
includes taxes & fees
1 Jan - 2 Jan 2026
Complete 1BR Home Sum

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is AU$2,054
includes taxes & fees
5 Jan - 6 Jan 2026
ENVITAE Hotel 4 Bedroom Luxury Apartments

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is AU$254
includes taxes & fees
21 Jan - 22 Jan 2026
Sleek 1BR Apt w/ Laundry

Modern Studio Near UChicago

Modern Studio Near UChicago
Hyde Park
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
The price is AU$228
includes taxes & fees
5 Jan - 6 Jan 2026
Modern Studio Near UChicago

Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
Downers Grove
9.6 out of 10, Exceptional, (30)
"Great option for a relatively affordable place to stay near family."
United States
Erick B.
The price is AU$169
includes taxes & fees
19 Jan - 20 Jan 2026
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Modern 1BR in Historic HydePark

Modern 1BR in Historic HydePark
Hyde Park
8.4 out of 10, Very good, (14)
"The location couldn't be beat. The beds were super comfortable and the room was perfect for my husband and I. We'll definitely stay here again!"
United States
Lisa O.
The price is AU$254
includes taxes & fees
1 Jan - 2 Jan 2026
Modern 1BR in Historic HydePark

Sunny Studio in Heart of Ravenswood

Sunny Studio in Heart of Ravenswood
Uptown
9.4 out of 10, Exceptional, (6)
"Great neighborhood, easy check in/out. "
United States
Leah B.
The price is AU$228
includes taxes & fees
6 Jan - 7 Jan 2026
Sunny Studio in Heart of Ravenswood

Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago
Hyde Park
9.4 out of 10, Exceptional, (3)
"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."
United States
Alan F.
The price is AU$254
includes taxes & fees
5 Jan - 6 Jan 2026
Bright & Cozy 1BR Near UChicago
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

Find out more about Countryside

Everything you need to know about Countryside holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Countryside holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Countryside holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Countryside holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Countryside. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Countryside holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Countryside holiday rentals we have selected for you start as low as AU$128 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Countryside rentals

At Expedia, we put the best Countryside holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Countryside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Countryside holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Countryside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Countryside?

Yes, there are holiday rentals close to the most popular sights in Countryside, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Countryside has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Countryside offers a patio, a BBQ 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 Galloping Ghost, or get out into nature at a spot like Millennium Park. In the wider area, you’ll find popular places such as Michigan Avenue and Wrigley Field.

What are holiday rentals like in Countryside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Countryside. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for small groups.