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Countryside Holiday Rentals

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Our top choices for Countryside holiday rentals

1. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 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 NZ$248
includes taxes & fees
15 Nov - 16 Nov
Wrigleyville Suites

2. 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 NZ$316
includes taxes & fees
17 Nov - 18 Nov
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (92 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is NZ$415
includes taxes & fees
19 Nov - 20 Nov
Kasa Lake Shore Chicago

4. 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 NZ$457
includes taxes & fees
22 Nov - 23 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

5. 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.
The price is NZ$346
includes taxes & fees
16 Nov - 17 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5

6. 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 NZ$777
includes taxes & fees
30 Nov - 1 Dec
Chic Urban Retreat Near Wrigley Field w/Parking

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (76 reviews)
"Had an amazing stay and would definitely book again!"
United States
Makenna
The price is NZ$380
includes taxes & fees
17 Nov - 18 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking

8. Studio Near Wrigley • Sleeps 4 • Games • Fireplace

Studio Near Wrigley • Sleeps 4 • Games • Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"Clean, comfortable bed, plenty of amenities. Steps and entry were a little awkward. Street parking only unless you paid extra for their garage which was a very tight fit for my sedan. Note older building so could hear neighbors but it wasn’t intrusive. Also note 3.6 miles to Wrigley was a 25 minute drive. Overall great place and would stay again."
United States
Meagan C.
The price is NZ$486
includes taxes & fees
17 Nov - 18 Nov
Studio Near Wrigley • Sleeps 4 • Games • Fireplace

9. 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$149
includes taxes & fees
1 Dec - 2 Dec
2 Full Beds | Non-Smoking, Kitchen

10. 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 NZ$469
includes taxes & fees
17 Nov - 18 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

11. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is NZ$236
includes taxes & fees
10 Dec - 11 Dec
Cozy studio in Andersonville Chicago

12. 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 NZ$283
includes taxes & fees
15 Nov - 16 Nov
Hyde Park Trendy Studio Apartment in Good Spot

13. 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 NZ$1,187
includes taxes & fees
16 Nov - 17 Nov
Vibrant House, Walk to Train, Game Room

14. Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Uptown
8.8 out of 10, Excellent, (20 reviews)
"READ THE FULL LISTING BEFORE YOU BOOK!! I've never had to jump through so many hoops to book a room before! Then they reached out multiple times via Vrbo messaging, texting and now a phone call requesting a 5 star review. What a pain just for a room to sleep in after a concert at Wrigley!With that said, the space was great! Clean, comfy and looked to have all of the essentials should you need to use the apartment more than we did."
United States
Heather B.
The price is NZ$467
includes taxes & fees
17 Nov - 18 Nov
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

15. 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 NZ$385
includes taxes & fees
16 Nov - 17 Nov
3BR Complete and Spacious Apartment in Ideal Spot

16. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (563 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is NZ$410
includes taxes & fees
22 Nov - 23 Nov
Level Chicago – Old Town

17. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (289 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveller
The price is NZ$135
includes taxes & fees
1 Dec - 2 Dec
King Bed Non-Smoking

18. Air-Conditioned King Suite | Complimentary Breakfast

Air-Conditioned King Suite | Complimentary Breakfast
York Center
9.0 out of 10, Wonderful, (6 reviews)
"Very nice facility. Room was spacious and comfortable. Staff were friendly and helpful. Had a great experience. "
United States
Jeffery R.
The price is NZ$316
includes taxes & fees
22 Nov - 23 Nov
Air-Conditioned King Suite | Complimentary Breakfast

19. 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, (28 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$312
includes taxes & fees
15 Nov - 16 Nov
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

20. 1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.6 out of 10, Excellent, (14 reviews)
"good place to stay clean and comfortable!"
United States
patricia r.
The price is NZ$285
includes taxes & fees
17 Nov - 18 Nov
1BR/1BA City Comfort
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.