Photo by Monica Ferro

Countryside Holiday Rentals

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Holiday Rentals in Countryside

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is S$210
includes taxes & fees
26 Nov - 27 Nov
Sentral Michigan Avenue
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is S$101
includes taxes & fees
1 Dec - 2 Dec
Sonder Market Hall
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is S$196
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (332)
"Excellent stay. Excellent location. "
Kasa Magnificent Mile Chicago
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (101)
"Excellent place to stay! "
The Neighborhood Hotel-Little Italy
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is S$291
includes taxes & fees
8 Dec - 9 Dec
Level Chicago – Old Town
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (176)
"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...
The price is S$183
includes taxes & fees
18 Dec - 19 Dec
Found Chicago powered by Sonder
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (114)
"The room is really cute and has all the amenities (including washing machine and dishwasher). Staying for business though I could hear quite a lot of noise from other rooms which made sleeping difficult at night "
The price is S$215
includes taxes & fees
23 Dec - 24 Dec
Sonder The Burnham Apartments
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (233)
"Brilliant apartment, perfect for my 4 night stay while visiting for a conference. Well equipped, spacious and brilliant views. Check in was very smooth. Would recommend "
Kasa South Loop Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (132)
"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!"
The price is S$209
includes taxes & fees
16 Dec - 17 Dec
Sonder Jewelers Row
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (100)
"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!"
The price is S$137
includes taxes & fees
9 Dec - 10 Dec
Kasa River North Chicago
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (83)
"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."
The price is S$177
includes taxes & fees
23 Dec - 24 Dec
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.4 out of 10, Very good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is S$198
includes taxes & fees
23 Dec - 24 Dec
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (33)
"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...
The price is S$247
includes taxes & fees
17 Dec - 18 Dec
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.8 out of 10, Exceptional, (11)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
Ground Floor Studios in Chicago by 747 Lofts
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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Other types of properties in Countryside you may be interested in

Congress Plaza Hotel
Lobby

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8211)
"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 "
The price is S$158
includes taxes & fees
8 Dec - 9 Dec
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3574)
"Is very close to everything "
The price is S$153
includes taxes & fees
25 Dec - 26 Dec
River Hotel
Club Quarters Hotel, Central Loop, Chicago
Premium bedding, in-room safe, desk, laptop workspace

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3312)
"It was a great experience "
The price is S$152
includes taxes & fees
25 Dec - 26 Dec
Club Quarters Hotel, Central Loop, 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.
Beautiful view of the beach with palm trees

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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 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.