A vast wheat field under a cloudy sky.

Countryside Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Countryside vacation rentals

A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

1. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
$204 nightly
The price is $216
Nov 4 - Nov 5
Total with taxes and fees
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

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.
$170 nightly
The price is $182
Oct 14 - Oct 15
Total with taxes and fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

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

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (81 reviews)
"Excellent place to stay!"
United States
Alicia K.
$270 nightly
The price is $309
Oct 19 - Oct 20
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern building with the name 'SENIORAL' prominently displayed on the facade.

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,354 reviews)
"Nice room, will stay again, highly recommend:)"
United States
Reina
$183 nightly
The price is $215
Oct 26 - Oct 27
Total with taxes and fees
Sentral Michigan Avenue
Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

5. 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 traveler
$69 nightly
The price is $76
Oct 30 - Oct 31
Total with taxes and fees
2 Full Beds | Non-Smoking, Kitchen
Private kitchen

6. 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.
$198 nightly
The price is $222
Oct 20 - Oct 21
Total with taxes and fees
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

7. 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.
$169 nightly
The price is $180
Oct 12 - Oct 13
Total with taxes and fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Lake

8. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (55 reviews)
"Location is perfect"
United States
Mary
$229 nightly
The price is $272
Nov 5 - Nov 6
Total with taxes and fees
Kasa Lake Shore Chicago
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

9. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
$202 nightly
The price is $207
Oct 26 - Oct 27
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

10. 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
$211 nightly
The price is $242
Nov 2 - Nov 3
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
A living room with a brick fireplace, a flat-screen TV mounted above it, and a large potted plant.

11. 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.
$185 nightly
The price is $197
Oct 12 - Oct 13
Total with taxes and fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
A modern living room with teal sofas, a coffee table, and a TV.

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, (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.
$150 nightly
The price is $160
Oct 12 - Oct 13
Total with taxes and fees
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
A modern living room with a blue sofa, a patterned rug, and a television.

13. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
$194 nightly
The price is $218
Oct 13 - Oct 14
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

14. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (8 reviews)
"Great location and easy on street parking. "
United States
Lori A.
$257 nightly
The price is $304
Oct 26 - Oct 27
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
A modern kitchen with a large island, bar stools, and a city view.

15. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (535 reviews)
"Location and facility was very nice"
United States
Brian
$278 nightly
The price is $327
Nov 2 - Nov 3
Total with taxes and fees
Level Chicago – Old Town
A living room with a grey sofa, a white coffee table, and a grey rug.

16. Small hidden Gem. Location!

Small hidden Gem. Location!
Cicero
9.2 out of 10, Wonderful, (25 reviews)
"Great viby place really enjoyed staying here"
United States
Edward S.
$218 nightly
The price is $233
Nov 2 - Nov 3
Total with taxes and fees
Small hidden Gem. Location!
Terrace/patio

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
$289 nightly
The price is $330
Oct 25 - Oct 26
Total with taxes and fees
At Home in Oak Park
A modern bedroom with a bed, a sofa, and a hanging plant.

18. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (100 reviews)
"Great location and amazing space! Perfect for visiting the city to apartment search for an upcoming move."
United States
Audrey A.
$113 nightly
The price is $139
Oct 26 - Oct 27
Total with taxes and fees
Cozy studio in Andersonville Chicago
Private kitchen

19. 1BR Apartment - Walk to Shops - Downtown OAK PARK

1BR Apartment - Walk to Shops - Downtown OAK PARK
Oak Park
9.2 out of 10, Wonderful, (44 reviews)
"Great location! Enjoyed my stay!"
United States
Shannon H.
$223 nightly
The price is $255
Oct 27 - Oct 28
Total with taxes and fees
1BR Apartment - Walk to Shops - Downtown OAK PARK
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

20. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
$344 nightly
The price is $368
Oct 7 - Oct 8
Total with taxes and fees
LUXE 3 BR, 2 BA + Hot Tub
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
"A beautiful old hotel that is conveniently located. No frills."
Jenna 4-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Countryside

Everything you need to know about Countryside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Countryside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Countryside vacation 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 low season months. For more hustle and bustle, you may prefer to visit Countryside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $72 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Countryside rentals

At Expedia, we put the best Countryside vacation 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 vacation.

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.

Explore a world of travel with Expedia

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 Childrens Museum of Oak Lawn, or get out into nature at a spot like Millennium Park. In the larger area, you’ll find popular places like Soldier Field and Navy Pier.

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.