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Countryside Holiday Rentals

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Our top choices for Countryside holiday rentals

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 NZ$333
includes taxes & fees
13 Sept - 14 Sept
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

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 NZ$306
includes taxes & fees
17 Aug - 18 Aug
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

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, (32 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 NZ$511
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,265 reviews)
"The room and building were beautiful and located in a great place."
United States
Ryan
The price is NZ$353
includes taxes & fees
30 Aug - 31 Aug
Sentral Michigan Avenue

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

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (69 reviews)
"Very nice stay. Close to everything. Host very helpful. "
United States
Tamela S.
The price is NZ$434
includes taxes & fees
18 Aug - 19 Aug
Chic Suite/Mins to L Train /Laundry/Free Parking

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 NZ$544
includes taxes & fees
18 Aug - 19 Aug
Cozy, Comfortable and Convenient apartment. Close to everything!

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 NZ$508
includes taxes & fees
10 Sept - 11 Sept
Kasa Lake Shore Chicago

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

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 traveller
The price is NZ$138
includes taxes & fees
12 Sept - 13 Sept
Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago

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 NZ$309
includes taxes & fees
10 Sept - 11 Sept
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

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)
The price is NZ$478
includes taxes & fees
7 Sept - 8 Sept
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

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 NZ$531
includes taxes & fees
19 Aug - 20 Aug
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

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 NZ$642
includes taxes & fees
16 Aug - 17 Aug
LUXE 3 BR, 2 BA + Hot Tub

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 NZ$874
includes taxes & fees
9 Sept - 10 Sept
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

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

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 NZ$750
includes taxes & fees
24 Aug - 25 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.4 out of 10, Exceptional, (6 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is NZ$670
includes taxes & fees
19 Aug - 20 Aug
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

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 NZ$1,011
includes taxes & fees
18 Aug - 19 Aug
4BR Retreat w/ Theater, Arcade, Gym and Firepit

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 NZ$546
includes taxes & fees
1 Sept - 2 Sept
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

Find out more about Countryside

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Countryside holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Countryside. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Countryside. Seeing all the best attractions is bound to make you fall in love with Countryside. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Countryside short-term rentals, that won’t be hard to do.

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.