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Countryside Holiday Rentals

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Our top choices for Countryside holiday rentals

Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
The price is AU$530
includes taxes & fees
4 Aug - 5 Aug
Kasa Lake Shore Chicago

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,208 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is AU$353
includes taxes & fees
9 Aug - 10 Aug
Sentral Michigan Avenue

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,686
includes taxes & fees
18 July - 19 July
Modern 3BR Apartment Near North Ave Shops

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (8 reviews)
"Excellent, clean, modern, fully furnished apartment in downtown Chicago that is a short car ride or walk to anything you need or want to visit. The neighborhood and building are very safe and the covered parking is well worth the extra expense. We loved the extra space to spread out and the skyline views were beautiful at night. The staff responded right away to any questions we had and even helped to accommodate us an extra night when an event kept us in town longer. The beds were comfortable...
United States
Kathryn
The price is AU$1,256
includes taxes & fees
10 July - 11 July
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (500 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is AU$629
includes taxes & fees
9 Aug - 10 Aug
Level Chicago – Old Town

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
The price is AU$427
includes taxes & fees
13 July - 14 July
The Oak Park Loft

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (24 reviews)
"Great location. "
United States
Tom S.
The price is AU$1,363
includes taxes & fees
2 Aug - 3 Aug
Modern West Loop Gem-City Views & Prime Location 6

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (62 reviews)
"Our stay was very comfortable. Communication was fantastic and super timely. The kitchen was well stocked. The house was very clean and spacious. Would definitely stay there again!"
United States
Erin B.
The price is AU$573
includes taxes & fees
15 July - 16 July
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is AU$500
includes taxes & fees
10 July - 11 July
LIVN West Loop Chicago King Studio

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"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$868
includes taxes & fees
26 July - 27 July
River North Rooftop With In and Out Parking 3

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (816 reviews)
"Great place to stay."
United States
Benedictine
The price is AU$579
includes taxes & fees
21 July - 22 July
Kasa Magnificent Mile Chicago

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (77 reviews)
"The host responded quickly to my requests. Apartment was clean. Kitchen well stocked with cooking, utensils, spices, etc. He registered my car so I coiud park on the street without any problem. Close to the Blue Line stop to take the "L" into downtown Chicago."
United States
Michael
The price is AU$480
includes taxes & fees
13 July - 14 July
Cozy, Comfortable and Convenient apartment. Close to everything!

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is AU$986
includes taxes & fees
10 July - 11 July
South Loop Rooftop With In & Out Parking 1

4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
The price is AU$1,061
includes taxes & fees
14 July - 15 July
4BR Retreat w/ Theater, Arcade, Gym and Firepit

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (26 reviews)
"Great location, close to public transport and Whole Foods. The property was clean, quiet, and easy to access. The host was great with communication. We would stay again! "
United States
Susan R.
The price is AU$2,607
includes taxes & fees
31 July - 1 Aug
Spacious 4BR Central Apartment w/ Skyline Views

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is AU$507
includes taxes & fees
12 July - 13 July
LIVN Millennium Park Downtown Chicago 2BR

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (69 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is AU$457
includes taxes & fees
29 July - 30 July
✽ Charming Cottage ✽ close to College/Town/Station

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (102 reviews)
"Everything was good!"
United States
Brio
The price is AU$469
includes taxes & fees
13 July - 14 July
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (11 reviews)
"Amazing property had everything we need! "
United States
Rachel
The price is AU$622
includes taxes & fees
12 July - 13 July
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
7.6 out of 10, Good, (12 reviews)
The price is AU$639
includes taxes & fees
16 July - 17 July
Cozy apartment with AC and WiFi in awesome Chicago
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$353 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Countryside is located in the city centre, and has a balcony, a BBQ 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 that you can cook with friends or family.

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 Grant Park. In the wider area, you’ll find popular places such as United Center and Soldier 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.