Countryside Holiday Rentals

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Our top choices for Countryside holiday rentals

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is AU$361
includes taxes & fees
20 May - 21 May
Chic Studio in the Heart of the Gold Coast

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,160 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is AU$286
includes taxes & fees
25 May - 26 May
Sentral Michigan Avenue

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
The price is AU$604
includes taxes & fees
27 May - 28 May
Modern 3BR Apartment Near North Ave Shops

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
9.8 out of 10, Exceptional, (10 reviews)
"Room was clean, check in was easy, and the owner was very communicative."
United States
David
The price is AU$250
includes taxes & fees
19 May - 20 May
Cozy Charm Studio Apt in Chicago

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is AU$403
includes taxes & fees
20 May - 21 May
West Loop Living – Bright 1BR

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, (7 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
The price is AU$806
includes taxes & fees
20 May - 21 May
Modern West Loop Gem-City Views & Prime Location 3

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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 AU$497
includes taxes & fees
21 May - 22 May
Sunlit 1BR Apartment | Warm & Welcoming Space

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (72 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is AU$474
includes taxes & fees
20 May - 21 May
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

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, (5 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 AU$823
includes taxes & fees
26 May - 27 May
River North Rooftop With In and Out Parking 3

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, (63 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
The price is AU$316
includes taxes & fees
19 May - 20 May
Chic Suite/Mins to L Train /Laundry/Free Parking

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (477 reviews)
"Love the amenities. Great location too"
United States
Paul
The price is AU$329
includes taxes & fees
26 May - 27 May
Level Chicago – Old Town

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (74 reviews)
"Nice, clean, safe house."
United States
Adrienne P.
The price is AU$469
includes taxes & fees
20 May - 21 May
Cozy, Comfortable and Convenient apartment. Close to everything!

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is AU$653
includes taxes & fees
20 May - 21 May
Spacious 4BR Central Apartment w/ Skyline Views

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, (12 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is AU$183
includes taxes & fees
20 May - 21 May
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.2 out of 10, Wonderful, (7 reviews)
"It was really a great place. Bb oo"
United States
Kate S.
The price is AU$250
includes taxes & fees
19 May - 20 May
Trendy & Comfy Studio Unit

Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location
Hyde Park
9.6 out of 10, Exceptional, (4 reviews)
"Location was just perfect!"
United States
Meg D.
The price is AU$258
includes taxes & fees
19 May - 20 May
Studio Unit | Chic + Prime Location

Cozy Well-Equipped Studio Apartment

Cozy Well-Equipped Studio Apartment
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Wow, this is a wonderful Place to stay. The host Is very responsive and friendly The apartment is immaculate I recommend this place highly . "
United States
pnina
The price is AU$289
includes taxes & fees
20 May - 21 May
Cozy Well-Equipped Studio Apartment

Vibrant 1BR Apartment

Vibrant 1BR Apartment
Lakeview
9.8 out of 10, Exceptional, (7 reviews)
"Great place. Host was very informative. "
United States
Cheryl S.
The price is AU$307
includes taxes & fees
19 May - 20 May
Vibrant 1BR Apartment

Sunlit & Chic 2BR Retreat

Sunlit & Chic 2BR Retreat
Hyde Park
10.0 out of 10, Exceptional, (4 reviews)
"Great location in Hyde Park! Super clean and comfortable. Bus stop by the front door and walkable to so many things we wanted to do! "
United States
Allison K.
The price is AU$347
includes taxes & fees
19 May - 20 May
Sunlit & Chic 2BR Retreat

Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
9.6 out of 10, Exceptional, (7 reviews)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is AU$359
includes taxes & fees
18 May - 19 May
Comfortable 2BR Chicago Apt
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, 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$286 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This holiday home rental outside of Countryside is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable 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 Grant Park. In the wider area, you’ll find popular places such as Navy Pier 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.