Countryside Holiday Rentals from €72: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Countryside has to offer?

LUXE 3 BR, 2 BA + Hot Tub : This holiday home rental outside of Countryside has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

Check Countryside holiday rental availability

Holiday Rentals in Countryside

"Great stay. Will stay again!"

includes taxes & fees

26 Nov - 27 Nov

"Easiest check in and check out process "

includes taxes & fees

1 Dec - 2 Dec

Superior Apartment, 1 Bedroom, Balcony, City View | Living area

"Nice"

includes taxes & fees

19 Dec - 20 Dec

49-inch Smart TV with digital channels, TV, streaming services

"Excellent stay. Excellent location. "

50-inch Smart TV with satellite channels

"Excellent place to stay! "

"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"

includes taxes & fees

8 Dec - 9 Dec

"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...

includes taxes & fees

16 Dec - 17 Dec

"Absolutely loved everything about the location of the Sonder and everything Chicago has to offer , highly recommend and was truly impressed by Chicago, the feel of Chicago the people the entire city was perfect, thank you kindly "

includes taxes & fees

23 Dec - 24 Dec

42-inch Smart TV with digital channels, TV, streaming services

"Amazing stay!"

Free toiletries, hair dryer, towels, soap

"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"

includes taxes & fees

16 Dec - 17 Dec

"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"

includes taxes & fees

8 Dec - 9 Dec

"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."

includes taxes & fees

23 Dec - 24 Dec

"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"

"Good location clean"

"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "

includes taxes & fees

23 Dec - 24 Dec

"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "

"Excited about our trip to Chicago and was not disappointed. Communication was very good from the homeowner location is perfect we had a fantastic time would recommend this for anyone wanting to enjoy downtown Chicago"

"Our family stayed for a corporate training and we had a great experience. The neighborhood wasn't the best but we felt very secure with having a garage to use. Very thankful for the quick communication! from the p "

"This little apartment is close to my cousin in Wrigleyville and a perfect location to get downtown and to see a Bears game (they are terrible right now). Entry instructions were easy and apartment was very clean."

40-inch flat-screen TV with digital channels, TV

"Everything was Excellent! The property was beautiful and most of all very CLEAN!!! The way everything was set up on site , to check-in and check-out was a very seamless process. The property was also very spacious, the beds were very big in size, super comfy, and having the three bathrooms in each bedroom was a such a plus. Greek neighborhood was a wonderful and smart location, everything is walking distance: for any coffee connoisseurs: Ground up Coffee is superb, Target is only a couple blocks...

includes taxes & fees

17 Dec - 18 Dec

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"Overall we liked the room we stayed at the only complaint was that the hallway leading to the room had an awful smell like lake dead fish or something when we arrived on 11/23 this morning the smell was less but it still smelled "

includes taxes & fees

8 Dec - 9 Dec

"The Hotel needs to get its iwn parking for sure it never stayed we had to walk 2 blocks that was terrible "

includes taxes & fees

25 Dec - 26 Dec

"The staff are very accommodating in allowing for early luggage drop off before check in and after checking out. Super convenient to local transit and Amtrak Chicago Union Station."

includes taxes & fees

25 Dec - 26 Dec

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, apart-hotels, 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 favorite 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 depends 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 €72 per night. Entering your travel dates in the search wizard you might find 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.

Recent reviews of Countryside properties

5/5 Excellent

"The room was comfortable with a beautiful view of the riverwalk, the staff was friendly and the location is convenient. "

A verified traveller stayed at The Royal Sonesta Chicago Downtown

Posted 4 hours ago

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?

LUXE 3 BR, 2 BA + Hot Tub: This holiday home rental outside of Countryside has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 Soldier Field and Millennium Park.

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.

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Holiday Rentals in Countryside

Check Countryside holiday rental availability

Holiday Rentals in Countryside

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Luxury Home Away From Your Home

Walking distance to restaurants, shops and Lake Michigan,

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LakeHouse

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Experience Chicago living near United Center

Wrigley/Southport Corridor Garden Oasis +parking!

Sonder Greektown

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Find out more about Countryside

Recent reviews of Countryside properties

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Frequently asked questions