Countryside Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Countryside vacation rentals

TV, offices

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 ￥17,829
￥36,991 total
includes taxes & fees
Mar 16 - Mar 17
Sun-Drenched 1BR Apartment
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ￥17,829
￥36,991 total
includes taxes & fees
Mar 16 - Mar 17
Modern Comfort: 1BR Unit w/ Laundry
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,103 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is ￥18,654
￥26,530 total
includes taxes & fees
Mar 19 - Mar 20
Sentral Michigan Avenue
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (709 reviews)
"Perfect location and very clean! "
United States
Latoya
Kasa Magnificent Mile Chicago
Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is ￥15,210
￥37,290 total
includes taxes & fees
Mar 18 - Mar 19
A quiet stay while you are away
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (441 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is ￥17,829
￥36,991 total
includes taxes & fees
Mar 16 - Mar 17
West Loop Living – Bright 1BR
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)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is ￥17,838
￥34,653 total
includes taxes & fees
Mar 11 - Mar 12
Chic Studio in the Heart of the Gold Coast
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, (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 ￥30,783
￥71,211 total
includes taxes & fees
Mar 18 - Mar 19
River North Rooftop With In and Out Parking 3
Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great place Great location "
United States
Josh W.
The price is ￥22,697
￥59,897 total
includes taxes & fees
Mar 11 - Mar 12
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Interior

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.
Premium Urban 4BR - Perfect Mix of Comfort & Location
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, (4 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is ￥14,997
￥19,422 total
includes taxes & fees
Mar 12 - Mar 13
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Property grounds

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, (60 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ￥18,328
￥47,545 total
includes taxes & fees
Mar 11 - Mar 12
2-bedroom apartment just 2 minutes drive to Wrigley Field
1 bedroom, iron/ironing board, travel crib, WiFi

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is ￥10,887
￥27,692 total
includes taxes & fees
Mar 16 - Mar 17
Charming Sunlit 1BR Apartment
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (57 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is ￥25,245
￥53,279 total
includes taxes & fees
Mar 16 - Mar 17
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Fridge, microwave, oven, stovetop

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Interior

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 ￥17,837
￥37,351 total
includes taxes & fees
Apr 5 - Apr 6
Pine Beam Sloth Apartment next to Blue Line
TV

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (27 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is ￥10,887
￥27,692 total
includes taxes & fees
Mar 16 - Mar 17
Nice 1BR Spot, Unwind & Relax
Paper towels

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (15 reviews)
"Very nice place to stay in secure neighborhood "
United States
Christina F.
The price is ￥23,667
￥42,367 total
includes taxes & fees
Mar 29 - Mar 30
Just remodeled apartment close to airport and mall
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ￥22,416
￥42,570 total
includes taxes & fees
Mar 23 - Mar 24
1BR Modern Luxe Apt with In-Unit Laundry
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

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

8/10 Good
"Clean room and business family budget "
HABIB 1-night trip
Posted 4 hours ago
Hilton Chicago O'Hare Airport

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?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This vacation home rental near Countryside is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Michigan Avenue 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.