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Countryside Vacation Rentals

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Our top choices for Countryside vacation rentals

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,410 reviews)
"Great for extended stays."
United States
Jeff
The price is CA $270
CA $317 total
includes taxes & fees
Nov 24 - Nov 25
Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (88 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is CA $215
CA $339 total
includes taxes & fees
Nov 25 - Nov 26
Kasa Lake Shore Chicago

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (560 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is CA $235
CA $311 total
includes taxes & fees
Nov 23 - Nov 24
Level Chicago – Old Town

4. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is CA $410
CA $1,010 total
includes taxes & fees
Nov 15 - Nov 16
Vibrant House, Walk to Train, Game Room

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (49 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is CA $208
CA $244 total
includes taxes & fees
Nov 11 - Nov 12
Wrigleyville Suites

6. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (35 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 CA $101
CA $247 total
includes taxes & fees
Nov 16 - Nov 17
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

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, (83 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is CA $152
CA $398 total
includes taxes & fees
Nov 11 - Nov 12
Cozy, Comfortable and Convenient apartment. Close to everything!

8. 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
9.6 out of 10, Exceptional, (7 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is CA $240
CA $367 total
includes taxes & fees
Nov 11 - Nov 12
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

9. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
"Great location with parking included"
United States
Melissa
The price is CA $288
CA $486 total
includes taxes & fees
Nov 12 - Nov 13
At Home in Oak Park

10. 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, (27 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 CA $212
CA $245 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

11. 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.
Great Area Logan Square Apt Games Pets - Sleeps 5

12. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (25 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
The price is CA $104
CA $284 total
includes taxes & fees
Nov 11 - Nov 12
3BR Complete and Spacious Apartment in Ideal Spot

13. Perfect 2-bedroom apartment in lovely Berwyn for your stay

Perfect 2-bedroom apartment in lovely Berwyn for your stay
Berwyn
The price is CA $143
CA $371 total
includes taxes & fees
Nov 15 - Nov 16
Perfect 2-bedroom apartment in lovely Berwyn for your stay

14. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (79 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
The price is CA $145
CA $608 total
includes taxes & fees
Nov 11 - Nov 12
Chic Urban Retreat Near Wrigley Field w/Parking

15. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is CA $175
CA $437 total
includes taxes & fees
Nov 14 - Nov 15
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

16. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is CA $302
CA $503 total
includes taxes & fees
Nov 19 - Nov 20
Historic Oak Park Home

17. 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 CA $106
CA $117 total
includes taxes & fees
Dec 9 - Dec 10
2 Full Beds | Non-Smoking, Kitchen

18. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (65 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is CA $254
CA $500 total
includes taxes & fees
Nov 16 - Nov 17
LUXE 3 BR, 2 BA + Hot Tub

19. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location could not be beat of looking to be near University of Chicago. Within walking distance to several restaurants, coffee, shops, and stores. Perfect for our trip!"
United States
rebecca
The price is CA $106
CA $230 total
includes taxes & fees
Nov 15 - Nov 16
Hyde Park Trendy Studio Apartment in Good Spot

20. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is CA $106
CA $367 total
includes taxes & fees
Nov 11 - Nov 12
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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.