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Countryside Holiday Rentals

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Our top choices for Countryside holiday rentals

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
9.2 out of 10, Wonderful, (21 reviews)
"Great little place not far from downtown. Clean apartment and a comfortable bed. Daughter slept on the couch and said it wasn't too bad. Everything worked as expected with no issues. Can hear people walking up the steps from time to time but overall pretty quiet. Took some time to find a parking spot but not the host's fault. Overall a great experience and would stay again."
United States
Garrett C.
The price is NZ$298
includes taxes & fees
30 Sept - 1 Oct
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

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, (33 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$318
includes taxes & fees
13 Oct - 14 Oct
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

3. Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Berwyn
9.4 out of 10, Exceptional, (25 reviews)
"A very comfy older building that has been upgraded in several areas. Convenient to transportation, restaurants and local events. "
United States
Carrie
The price is NZ$317
includes taxes & fees
30 Sept - 1 Oct
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

4. 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, (71 reviews)
"Easy access to the Green Line."
United States
Michael
The price is NZ$438
includes taxes & fees
27 Oct - 28 Oct
Chic Suite/Mins to L Train /Laundry/Free Parking

5. Experience Forest Park living near Top Places like downtown Chicago

Experience Forest Park living near Top Places like downtown Chicago
Forest Park
9.4 out of 10, Exceptional, (18 reviews)
"Good location for visiting family just outside Chicago."
United States
Josh H.
Experience Forest Park living near Top Places like downtown Chicago

6. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.8 out of 10, Exceptional, (23 reviews)
"Great place to stay "
United States
Harquesha S.
The price is NZ$317
includes taxes & fees
6 Oct - 7 Oct
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

7. Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.2 out of 10, Wonderful, (41 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
The price is NZ$343
includes taxes & fees
30 Sept - 1 Oct
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

8. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (80 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is NZ$538
includes taxes & fees
30 Sept - 1 Oct
Cozy, Comfortable and Convenient apartment. Close to everything!

9. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (63 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is NZ$651
includes taxes & fees
30 Sept - 1 Oct
LUXE 3 BR, 2 BA + Hot Tub

10. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
9.2 out of 10, Wonderful, (30 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveller
The price is NZ$141
includes taxes & fees
18 Oct - 19 Oct
2 Full Beds | Non-Smoking, Kitchen

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, (25 reviews)
"The room was very clean, and the host was timely with communications. The couches and bed were so comfy!"
United States
Kaitlyn W.
The price is NZ$283
includes taxes & fees
30 Sept - 1 Oct
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

12. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is NZ$1,031
includes taxes & fees
5 Oct - 6 Oct
Theater • Game Room • Gym • Firepit • 4BR Home

13. 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
7.8 out of 10, Good, (34 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is NZ$531
includes taxes & fees
30 Sept - 1 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

14. 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, (114 reviews)
"Very clean, spacious living area, and convenient location"
United States
Clara B.
The price is NZ$534
includes taxes & fees
5 Oct - 6 Oct
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

15. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is NZ$498
includes taxes & fees
8 Oct - 9 Oct
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

16. 2MI to Obama Center - Pet-Friendly near UOC!

2MI to Obama Center - Pet-Friendly near UOC!
Woodlawn
9.6 out of 10, Exceptional, (4 reviews)
"Great host very accommodating."
United States
Kali P.
The price is NZ$614
includes taxes & fees
1 Oct - 2 Oct
2MI to Obama Center - Pet-Friendly near UOC!

17. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is NZ$646
includes taxes & fees
6 Oct - 7 Oct
At Home in Oak Park

18. King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Lockport
10.0 out of 10, Exceptional, (10 reviews)
"We had a great stay. The host communicated well, property was clean, well stocked, and had plenty of space. If we were visiting this area again we would definitely stay here."
United States
Jennifer A.
The price is NZ$456
includes taxes & fees
28 Oct - 29 Oct
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is NZ$704
includes taxes & fees
6 Oct - 7 Oct
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
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 Childrens Museum of Oak Lawn, or get out into nature at a spot like Millennium Park. In the wider area, you’ll find popular places such as Soldier Field and Navy Pier.

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.