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Countryside Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Countryside holiday rentals

Dining

1. Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Berwyn
9.0 out of 10, Wonderful, (18 reviews)
"It's a great place to stay, honestly, the hosts are nice and there to help you as well.The place is big, it has good A/C, and lots of space for different activities.Finally, there's lots of parking available in case you are using a car."
United States
Juan Pablo T.
The price is HK$531
HK$1,323 total
includes taxes & fees
10 Aug - 11 Aug
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Smart TV, books

2. 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 HK$904
HK$2,058 total
includes taxes & fees
18 Aug - 19 Aug
Chic Suite/Mins to L Train /Laundry/Free Parking
Indoor pool

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,241 reviews)
"Great property and location."
United States
Michael
The price is HK$1,249
HK$1,696 total
includes taxes & fees
30 Aug - 31 Aug
Sentral Michigan Avenue
Smart TV

4. 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 HK$1,165
HK$2,362 total
includes taxes & fees
10 Aug - 11 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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 HK$1,532
HK$3,645 total
includes taxes & fees
10 Aug - 11 Aug
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Dining

6. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (53 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is HK$1,483
HK$3,013 total
includes taxes & fees
16 Aug - 17 Aug
LUXE 3 BR, 2 BA + Hot Tub
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 HK$988
HK$2,524 total
includes taxes & fees
18 Aug - 19 Aug
Cozy, Comfortable and Convenient apartment. Close to everything!
1 bedroom

8. 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 traveller
The price is HK$608
HK$672 total
includes taxes & fees
4 Sept - 5 Sept
Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago
Coffee/tea maker, fridge, microwave, oven

9. *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 HK$1,454
HK$3,121 total
includes taxes & fees
10 Aug - 11 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Lake

10. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.6 out of 10, Good, (11 reviews)
"Great location and super clean!"
United States
Erica
The price is HK$1,930
HK$2,761 total
includes taxes & fees
8 Sept - 9 Sept
Kasa Lake Shore Chicago
Interior

11. 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, (107 reviews)
"Very clean, spacious living area, and convenient location"
United States
Clara B.
The price is HK$1,186
HK$2,409 total
includes taxes & fees
11 Aug - 12 Aug
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Smart TV, video games, table football, ping pong

12. 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 HK$2,285
HK$6,165 total
includes taxes & fees
23 Aug - 24 Aug
Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home
Interior

13. 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, (21 reviews)
"Great host and had everything you would need."
United States
Mj2green J.
The price is HK$1,177
HK$1,435 total
includes taxes & fees
18 Aug - 19 Aug
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Outdoor dining

14. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.6 out of 10, Exceptional, (33 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
The price is HK$1,532
HK$3,004 total
includes taxes & fees
9 Aug - 10 Aug
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Full-sized fridge, microwave, oven, stovetop

15. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (514 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is HK$1,847
HK$2,361 total
includes taxes & fees
31 Aug - 1 Sept
Level Chicago – Old Town
Dining

16. 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 HK$601
HK$3,018 total
includes taxes & fees
11 Aug - 12 Aug
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Smart TV, fireplace

17. Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts

Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts
Lombard
9.4 out of 10, Exceptional, (23 reviews)
"The place was clean and wonderfull. Love the area."
United States
Jack W.
The price is HK$1,676
HK$2,956 total
includes taxes & fees
17 Aug - 18 Aug
Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts
Exterior

18. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (70 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is HK$1,412
HK$2,502 total
includes taxes & fees
6 Sept - 7 Sept
✽ Charming Cottage ✽ close to College/Town/Station
Interior

19. 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.
The price is HK$1,961
HK$4,787 total
includes taxes & fees
12 Aug - 13 Aug
Vintage Urban Retreat
TV

20. 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 HK$3,100
HK$7,579 total
includes taxes & fees
14 Aug - 15 Aug
4BR Retreat w/ Theater, Arcade, Gym and Firepit
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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"nice environment"
Aziza 1-night trip
Posted 3 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Countryside

Search for holiday rentals in Countryside on Expedia! You can easily find your home rentals, villas, holiday apartments in Countryside using one of the methods below:

  • View our selection of featured holiday rentals in Countryside
  • Use the map to find apartments and other holiday homes in the Countryside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Countryside while they last

Look no further and take a look at our great range of rental properties in Countryside!

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.