A vast wheat field under a cloudy sky.

Countryside Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Countryside holiday rentals

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,282 reviews)
"Nice stay"
United States
Heather
The price is AU$289
includes taxes & fees
8 Sept - 9 Sept
Sentral Michigan Avenue

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

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.4 out of 10, Exceptional, (39 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
The price is AU$277
includes taxes & fees
26 Aug - 27 Aug
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

3. 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 AU$502
includes taxes & fees
2 Sept - 3 Sept
LUXE 3 BR, 2 BA + Hot Tub

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
7.8 out of 10, Good, (33 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 AU$418
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (18 reviews)
"Great location and super clean!"
United States
Erica
The price is AU$386
includes taxes & fees
9 Sept - 10 Sept
Kasa Lake Shore 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 AU$361
includes taxes & fees
1 Sept - 2 Sept
Chic Suite/Mins to L Train /Laundry/Free Parking

7. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
9.8 out of 10, Exceptional, (28 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveller
The price is AU$121
includes taxes & fees
18 Sept - 19 Sept
2 Full Beds | Non-Smoking, Kitchen

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, (78 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is AU$484
includes taxes & fees
9 Sept - 10 Sept
Cozy, Comfortable and Convenient apartment. Close to everything!

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 AU$661
includes taxes & fees
30 Aug - 31 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

10. 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, (34 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 AU$447
includes taxes & fees
26 Aug - 27 Aug
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

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, (110 reviews)
"Very clean, spacious living area, and convenient location"
United States
Clara B.
The price is AU$418
includes taxes & fees
1 Sept - 2 Sept
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

12. 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, (23 reviews)
"Great host and had everything you would need."
United States
Mj2green J.
The price is AU$295
includes taxes & fees
1 Sept - 2 Sept
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

13. 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 AU$345
includes taxes & fees
7 Sept - 8 Sept
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

14. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is AU$478
includes taxes & fees
16 Sept - 17 Sept
The Oak Park Loft

15. 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 AU$511
includes taxes & fees
2 Sept - 3 Sept
Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts

16. Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (30 reviews)
"An incredible experience and wonderful place to stay. A perfect location, quiet, and my twin boys loved having their own spaces. Thank you so much!"
United States
Miriam B.
The price is AU$600
includes taxes & fees
31 Aug - 1 Sept
Spacious 4BR Central Apartment w/ Skyline Views

17. 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 AU$443
includes taxes & fees
1 Sept - 2 Sept
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

18. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.4 out of 10, Exceptional, (20 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is AU$296
includes taxes & fees
30 Aug - 31 Aug
LIVN West Loop Chicago Queen Superior Studio

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, (4 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is AU$741
includes taxes & fees
31 Aug - 1 Sept
4BR Retreat w/ Theater, Arcade, Gym and Firepit

20. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 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 AU$421
includes taxes & fees
31 Aug - 1 Sept
Level Chicago – Old Town
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Countryside Hotel Reviews

Find out more about Countryside

Everything you need to know about Countryside holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Countryside holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Countryside holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Countryside holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Countryside. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Countryside holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Countryside holiday rentals we have selected for you start as low as AU$206 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Countryside rentals

At Expedia, we put the best Countryside holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Countryside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Countryside holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Countryside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 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.