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Countryside Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Countryside vacation rentals

1 bedroom, desk, iron/ironing board, WiFi

1. Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Hickory Hills
9.6 out of 10, Exceptional, (8 reviews)
"Easy to locate shopping mall close by friendly neighborhood and safe. when you're looking at stay away from home that's where you want to be."
United States
Ralph
The price is SAR 469
SAR 783 total
includes taxes & fees
9 Sep - 10 Sep
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Dining

2. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
10.0 out of 10, Exceptional, (31 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is SAR 258
SAR 678 total
includes taxes & fees
17 Aug - 18 Aug
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Smart TV

3. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very Good, (31 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is SAR 558
SAR 1,139 total
includes taxes & fees
12 Aug - 13 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Exterior

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,250 reviews)
"Great property and location."
United States
Michael
The price is SAR 568
SAR 777 total
includes taxes & fees
30 Aug - 31 Aug
Sentral Michigan Avenue
Coffee/tea maker, fridge, microwave, oven

5. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.6 out of 10, Exceptional, (21 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is SAR 658
SAR 1,616 total
includes taxes & fees
12 Aug - 13 Aug
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Smart TV, books

6. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (68 reviews)
"Very nice stay. Close to everything. Host very helpful. "
United States
Tamela S.
The price is SAR 433
SAR 985 total
includes taxes & fees
17 Aug - 18 Aug
Chic Suite/Mins to L Train /Laundry/Free Parking
Coffee/tea maker, fridge, microwave, oven

7. 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 SAR 473
SAR 1,208 total
includes taxes & fees
18 Aug - 19 Aug
Cozy, Comfortable and Convenient apartment. Close to everything!
Lake

8. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (13 reviews)
"Great location and super clean!"
United States
Erica
The price is SAR 924
SAR 1,321 total
includes taxes & fees
7 Sep - 8 Sep
Kasa Lake Shore Chicago
Smart TV, video games, foosball, table tennis

9. Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home

Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is SAR 965
SAR 2,803 total
includes taxes & fees
23 Aug - 24 Aug
Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home
1 bedroom

10. Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago

Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago
Chicago
9.2 out of 10, Wonderful, (31 reviews)
"Nice, clean, and a quiet hotel"
United States
Anonymous traveler
The price is SAR 290
SAR 321 total
includes taxes & fees
4 Sep - 5 Sep
Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago
Interior

11. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (22 reviews)
"Great host and had everything you would need."
United States
Mj2green J.
The price is SAR 563
SAR 683 total
includes taxes & fees
12 Aug - 13 Aug
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Smart TV, video games

12. Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
The price is SAR 315
SAR 927 total
includes taxes & fees
12 Aug - 13 Aug
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Interior

13. 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, (110 reviews)
"Very clean, spacious living area, and convenient location"
United States
Clara B.
The price is SAR 561
SAR 1,171 total
includes taxes & fees
19 Aug - 20 Aug
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Dining

14. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (54 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is SAR 676
SAR 1,402 total
includes taxes & fees
24 Aug - 25 Aug
LUXE 3 BR, 2 BA + Hot Tub
Smart TV, computer monitors

15. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
O'Hare
10.0 out of 10, Exceptional, (2 reviews)
"The space was comfortable, clean and inviting.The host was fabulous! I recommend this place when visiting the Chicago area."
United States
Megan K.
The price is SAR 217
SAR 1,562 total
includes taxes & fees
12 Aug - 13 Aug
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
Interior

16. Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (15 reviews)
"It was a very nice neighborhood, with many restaurants and retail establishments in proximity. We really enjoyed our stay and our host was an excellent when it comes to communication."
United States
Tim P.
Vintage Urban Retreat
Coffee/tea maker, fridge, microwave, oven

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

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (63 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
United States
Joe M.
The price is SAR 834
SAR 1,668 total
includes taxes & fees
24 Aug - 25 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Dining

18. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.2 out of 10, Wonderful, (5 reviews)
"Excellent place to stay for a family trip. Lovely neighborhood. Check in was a breeze. Very responsive with any questions I had!"
United States
Traci
The price is SAR 334
SAR 1,530 total
includes taxes & fees
19 Aug - 20 Aug
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
TV

19. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (3 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is SAR 625
SAR 2,436 total
includes taxes & fees
17 Aug - 18 Aug
4BR Retreat w/ Theater, Arcade, Gym and Firepit
Exterior

20. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (3 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is SAR 666
SAR 1,239 total
includes taxes & fees
1 Sep - 2 Sep
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"I like having coffee available in the lobby when traveling. The coffee in the r room wasn’t good."
Todd 3-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown

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 Galloping Ghost, or get out into nature at a spot like Grant Park. In the larger area, you’ll find popular places like United Center and Soldier Field.

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.