Countryside Vacation Rentals

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Vacation Rentals in Countryside

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
$126 nightly
The price is $148
Dec 7 - Dec 8
Total with taxes and fees
Sentral Michigan Avenue
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (2)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
$145 nightly
The price is $159
Dec 7 - Dec 8
Total with taxes and fees
West Loop Living – Bright 1BR
Interior
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (4)
"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
$149 nightly
The price is $166
Jan 1 - Jan 2, 2026
Total with taxes and fees
Gold Coast Living: Modern Studio Unit
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$145 nightly
The price is $159
Dec 7 - Dec 8
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
$168 nightly
The price is $184
Dec 2 - Dec 3
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
TV, offices
Sun-Drenched 1BR Apartment

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (2)
"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.
$145 nightly
The price is $159
Dec 4 - Dec 5
Total with taxes and fees
Sun-Drenched 1BR Apartment
Interior
Your Chicago get Away

Apartment in Downtown Chicago

8.4 out of 10, Very Good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
$361 nightly
The price is $392
Dec 8 - Dec 9
Total with taxes and fees
Your Chicago get Away
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
$145 nightly
The price is $159
Dec 3 - Dec 4
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home
4 bedrooms, iron/ironing board, travel crib, WiFi
Modern West Loop Gem-City Views & Prime Location 3

Apartment in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (1)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
$168 nightly
The price is $197
Dec 30 - Dec 31
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 3
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stylish 1BR in West Loop
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
$254 nightly
The price is $299
Dec 3 - Dec 4
Total with taxes and fees
Chicago luxury home suites
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (390)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
$215 nightly
The price is $252
Dec 14 - Dec 15
Total with taxes and fees
Level Chicago – Old Town
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 1

Apartment in Downtown Chicago

9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
$291 nightly
The price is $316
Dec 7 - Dec 8
Total with taxes and fees
River North Rooftop With In and Out Parking 1
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
$347 nightly
The price is $407
Dec 5 - Dec 6
Total with taxes and fees
Kasa River North Chicago
Fridge, microwave, oven, stovetop
South Loop Rooftop With In and Out Parking 3

Apartment in Downtown Chicago

8.6 out of 10, Excellent, (4)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
$388 nightly
The price is $429
Dec 19 - Dec 20
Total with taxes and fees
South Loop Rooftop With In and Out Parking 3
TV, offices
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
$145 nightly
The price is $159
Dec 2 - Dec 3
Total with taxes and fees
Sleek 1BR Apt w/ Laundry
4 bedrooms, iron/ironing board, travel crib, WiFi
Modern West Loop Gem-City Views & Prime Location 5

Apartment in Downtown Chicago

2.0 star property
$135 nightly
The price is $158
Dec 17 - Dec 18
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 5
Iron/ironing board, travel crib, WiFi, bed sheets
Modern Studio Near UChicago

Apartment in Hyde Park

9.4 out of 10, Exceptional, (10)
"Clean room and convenient location! "
United States
Gabriela
$140 nightly
The price is $155
Dec 7 - Dec 8
Total with taxes and fees
Modern Studio Near UChicago
Fridge, microwave, dishwasher, coffee/tea maker
Modern West Loop Gem-City Views & Prime Location 2

Apartment in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (2)
"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "
United States
Erik R.
$231 nightly
The price is $270
Dec 30 - Dec 31
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 2
TV, offices
Bright & Cozy 1BR Near UChicago

Apartment in Hyde Park

10.0 out of 10, Exceptional, (2)
"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."
United States
Alan F.
$145 nightly
The price is $159
Dec 2 - Dec 3
Total with taxes and fees
Bright & Cozy 1BR Near UChicago
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

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"I enjoyed my stay with this hotel and would stay here again"
Kim Leticia Terrelle 4-night trip
Posted 3 hours ago
citizenM Chicago Downtown

Find out more about Countryside

Everything you need to know about Countryside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Countryside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Countryside vacation 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 low season months. For more hustle and bustle, you may prefer to visit Countryside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $91 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Countryside rentals

At Expedia, we put the best Countryside vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

LakeHouse: This vacation home rental near Countryside is located on the beach and has a fireplace, a balcony, 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 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.