Countryside Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Countryside vacation rentals

Desk, iron/ironing board, travel crib, WiFi

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 ￥24,128
￥43,272 total
includes taxes & fees
May 21 - May 22
Chic Studio in the Heart of the Gold Coast
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,165 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is ￥24,152
￥33,010 total
includes taxes & fees
May 25 - May 26
Sentral Michigan Avenue
Fitness facility

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
Modern 3BR Apartment Near North Ave Shops
Iron/ironing board, travel crib, WiFi, bed sheets

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 ￥13,652
￥29,434 total
includes taxes & fees
May 19 - May 20
Cozy Charm Studio Apt in Chicago
1 bedroom, iron/ironing board, travel crib, WiFi

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 ￥23,017
￥43,948 total
includes taxes & fees
May 25 - May 26
West Loop Living – Bright 1BR
Interior

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 ￥25,875
￥90,912 total
includes taxes & fees
May 20 - May 21
Modern West Loop Gem-City Views & Prime Location 3
TV, offices

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 ￥21,906
￥41,279 total
includes taxes & fees
May 26 - May 27
Sunlit 1BR Apartment | Warm & Welcoming Space
Property grounds

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, (73 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ￥22,732
￥54,296 total
includes taxes & fees
May 19 - May 20
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Interior

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 ￥43,019
￥97,956 total
includes taxes & fees
May 25 - May 26
River North Rooftop With In and Out Parking 3
Smart TV, books

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 ￥14,572
￥36,673 total
includes taxes & fees
May 19 - May 20
Chic Suite/Mins to L Train /Laundry/Free Parking
Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (477 reviews)
"Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again. "
Canada
Lissa
The price is ￥28,288
￥37,122 total
includes taxes & fees
May 26 - May 27
Level Chicago – Old Town
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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 ￥22,859
￥54,701 total
includes taxes & fees
May 20 - May 21
Cozy, Comfortable and Convenient apartment. Close to everything!
Exterior

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 ￥25,240
￥74,437 total
includes taxes & fees
May 20 - May 21
Spacious 4BR Central Apartment w/ Skyline Views
Interior

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 ￥16,509
￥21,058 total
includes taxes & fees
May 20 - May 21
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Iron/ironing board, travel crib, WiFi, bed sheets

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 ￥12,540
￥28,131 total
includes taxes & fees
May 26 - May 27
Trendy & Comfy Studio Unit
Iron/ironing board, travel crib, WiFi, bed sheets

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 ￥13,810
￥29,817 total
includes taxes & fees
May 19 - May 20
Studio Unit | Chic + Prime Location
Iron/ironing board, travel crib, WiFi, bed sheets

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 ￥16,826
￥33,152 total
includes taxes & fees
May 20 - May 21
Cozy Well-Equipped Studio Apartment
TV, offices

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 ￥15,874
￥33,624 total
includes taxes & fees
May 26 - May 27
Vibrant 1BR Apartment
2 bedrooms, iron/ironing board, travel crib, WiFi

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 ￥17,938
￥39,012 total
includes taxes & fees
May 18 - May 19
Sunlit & Chic 2BR Retreat
Interior

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 ￥18,890
￥40,128 total
includes taxes & fees
May 26 - May 27
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

Congress Plaza Hotel

Congress Plaza Hotel

6/10 Okay
"Did not look like the pictures shown online old hotel not update"
Marquita 2-night trip
Posted 3 hours ago
Congress Plaza Hotel

Find out more about Countryside

Search for holiday rentals in Countryside on Expedia! You can easily find your home rentals, villas, holiday apartments in Countryside using one of the methods below:

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Look no further and take a look at our great range of rental properties in Countryside!

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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This vacation home rental near Countryside is located in the city center and offers a barbecue grill, 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 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 larger area, you’ll find popular places like Navy Pier and Wrigley Field.

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.