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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 AED 492
AED 809 total
includes taxes & fees
11 Sep - 12 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 AED 252
AED 663 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 AED 545
AED 1,114 total
includes taxes & fees
18 Aug - 19 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Premium Apartment, 2 Bedrooms | Private kitchen | Coffee/tea maker, oven, stovetop, dishwasher

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,254 reviews)
"Great property and location."
United States
Michael
The price is AED 555
AED 760 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 AED 841
AED 1,831 total
includes taxes & fees
17 Aug - 18 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 AED 410
AED 928 total
includes taxes & fees
18 Aug - 19 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 AED 463
AED 1,182 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 AED 863
AED 1,244 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 AED 905
AED 2,714 total
includes taxes & fees
17 Aug - 18 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 AED 284
AED 314 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 AED 551
AED 668 total
includes taxes & fees
13 Aug - 14 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 AED 433
AED 1,049 total
includes taxes & fees
7 Sep - 8 Sep
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 AED 549
AED 1,145 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 AED 694
AED 1,403 total
includes taxes & fees
16 Aug - 17 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 AED 375
AED 1,746 total
includes taxes & fees
31 Aug - 1 Sep
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 AED 815
AED 1,632 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 AED 326
AED 1,496 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 AED 552
AED 2,298 total
includes taxes & fees
18 Aug - 19 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 AED 740
AED 1,323 total
includes taxes & fees
7 Sep - 8 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

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

10/10 Excellent
"Great stay"
Tochi 4-night trip
Posted less than an hour ago
Hyatt Regency McCormick Place Chicago

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.