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Our top choices for Countryside holiday rentals

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is £151
includes taxes & fees
29 Mar - 30 Mar
Modern Comfort: 1BR Unit w/ Laundry

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,114 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is £126
includes taxes & fees
1 Apr - 2 Apr
Sentral Michigan Avenue

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is £151
includes taxes & fees
29 Mar - 30 Mar
Sun-Drenched 1BR Apartment

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is £151
includes taxes & fees
29 Mar - 30 Mar
West Loop Living – Bright 1BR

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is £335
includes taxes & fees
30 Mar - 31 Mar
River North Rooftop With In and Out Parking 3

Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
9.2 out of 10, Wonderful, (17 reviews)
"Very cozy, amenities in great condition."
United States
Kaitlin T.
The price is £163
includes taxes & fees
29 Mar - 30 Mar
Cozy & Furnished 2BR Unit

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is £325
includes taxes & fees
15 Apr - 16 Apr
Premium Urban 4BR - Perfect Mix of Comfort & Location

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (65 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is £242
includes taxes & fees
29 Mar - 30 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is £186
includes taxes & fees
30 Mar - 31 Mar
The Oak Park Loft

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (29 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is £146
includes taxes & fees
30 Mar - 31 Mar
Nice 1BR Spot, Unwind & Relax

Stylish and Roomy 2BR in Chicago

Stylish and Roomy 2BR in Chicago
Edgewater
9.0 out of 10, Wonderful, (14 reviews)
"Clean room, easy, check-in, great location"
United States
brent w.
The price is £163
includes taxes & fees
29 Mar - 30 Mar
Stylish and Roomy 2BR in Chicago

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Great all around!!!"
United States
Kennedy L.
The price is £412
includes taxes & fees
22 Apr - 23 Apr
Modern West Loop Gem-City Views & Prime Location 3

Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
Downers Grove
9.6 out of 10, Exceptional, (32 reviews)
"Great option for a relatively affordable place to stay near family."
United States
Erick B.
The price is £103
includes taxes & fees
23 Apr - 24 Apr
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
The price is £186
includes taxes & fees
29 Mar - 30 Mar
Pine Beam Sloth Apartment next to Blue Line

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.4 out of 10, Good, (6 reviews)
"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."
United States
Darryl C.
The price is £149
includes taxes & fees
29 Mar - 30 Mar
Uptown Studio Gem Sum

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.4 out of 10, Exceptional, (66 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is £114
includes taxes & fees
31 Mar - 1 Apr
Cozy studio in Andersonville Chicago

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, (60 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
The price is £157
includes taxes & fees
31 Mar - 1 Apr
Chic Suite/Mins to L Train /Laundry/Free Parking

Bright Spaced 3BR Furnished Stay

Bright Spaced 3BR Furnished Stay
Portage Park
9.4 out of 10, Exceptional, (3 reviews)
"Quick communication, great value, clean & bright."
United States
Barb S.
The price is £182
includes taxes & fees
29 Mar - 30 Mar
Bright Spaced 3BR Furnished Stay

Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
9.0 out of 10, Wonderful, (8 reviews)
"Everything was good besides communication I felt like was nonexistent, but the issue was figured out :) "
United States
Wilber
The price is £210
includes taxes & fees
31 Mar - 1 Apr
Cozy apartment with AC and WiFi in awesome Chicago

Ideal 2BR Getaway Close to Attractions

Ideal 2BR Getaway Close to Attractions
Rogers Park
8.4 out of 10, Very good, (7 reviews)
"Host was fantastic and property excellent!"
United States
David R.
The price is £162
includes taxes & fees
31 Mar - 1 Apr
Ideal 2BR Getaway Close to Attractions
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

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, apart-hotels, 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 favorite 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 depends 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 £72 per night. Entering your travel dates in the search wizard you might find 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?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This holiday home rental outside of Countryside is located in the city centre, and has a balcony, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 3 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 Michigan Avenue and Wrigley Field.

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.