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Countryside Vacation Rentals

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Our top choices for Countryside vacation rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,197 reviews)
"Great location"
United States
JAVIER
The price is CA $236
CA $319 total
includes taxes & fees
Jul 1 - Jul 2
Sentral Michigan Avenue

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
United States
Emeline B.
The price is CA $390
CA $910 total
includes taxes & fees
Jul 8 - Jul 9
ENVITAE Hotel, 4BR Luxury Modern Apartments

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, (16 reviews)
"Great place! "
United States
Isabella T.
The price is CA $192
CA $365 total
includes taxes & fees
Jun 30 - Jul 1
Just remodeled apartment close to airport and mall

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is CA $313
CA $693 total
includes taxes & fees
Jul 15 - Jul 16
River North Rooftop With In and Out Parking 1

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $222
CA $301 total
includes taxes & fees
Jun 29 - Jun 30
LIVN West Loop Chicago Classic Queen Studio

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, (82 reviews)
"Great location for a short trip "
United States
Eric W.
The price is CA $226
CA $519 total
includes taxes & fees
Jul 6 - Jul 7
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (496 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is CA $343
CA $438 total
includes taxes & fees
Jun 30 - Jul 1
Level Chicago – Old Town

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (101 reviews)
"Everything was good!"
United States
Brio
The price is CA $214
CA $448 total
includes taxes & fees
Jul 6 - Jul 7
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
10.0 out of 10, Exceptional, (26 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveller
The price is CA $157
CA $173 total
includes taxes & fees
Jun 30 - Jul 1
2 Full Beds | Non-Smoking, Kitchen

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
The price is CA $237
CA $321 total
includes taxes & fees
Jun 29 - Jun 30
LIVN Millennium Park Downtown Chicago Prem Studio

Beautiful Unit CHI in Prime River North - 2

Beautiful Unit CHI in Prime River North - 2
Downtown Chicago
8.6 out of 10, Excellent, (25 reviews)
"Great place to stay for our girls weekend. Very convenient to everything in the city! We had the second unit and just to know this is a walk up with about 40-45 stairs to get to the unit. "
United States
Dawn P.
The price is CA $237
CA $637 total
includes taxes & fees
Jul 3 - Jul 4
Beautiful Unit CHI in Prime River North - 2

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (83 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is CA $199
CA $338 total
includes taxes & fees
Jul 9 - Jul 10
Cozy studio in Andersonville Chicago

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (77 reviews)
"The host responded quickly to my requests. Apartment was clean. Kitchen well stocked with cooking, utensils, spices, etc. He registered my car so I coiud park on the street without any problem. Close to the Blue Line stop to take the "L" into downtown Chicago."
United States
Michael
The price is CA $218
CA $508 total
includes taxes & fees
Jun 30 - Jul 1
Cozy, Comfortable and Convenient apartment. Close to everything!

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Lockport
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay. The property was nicely decorated-very modern and cute. The location was good for us-close to the friends and family we wanted to visit. We felt it was a very safe area. Stores and restaurants were close by. Definitely recommend and will stay there again!"
United States
Denise K.
The price is CA $154
CA $312 total
includes taxes & fees
Jun 30 - Jul 1
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (68 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is CA $256
CA $463 total
includes taxes & fees
Jul 26 - Jul 27
✽ Charming Cottage ✽ close to College/Town/Station

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

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (62 reviews)
"Our stay was very comfortable. Communication was fantastic and super timely. The kitchen was well stocked. The house was very clean and spacious. Would definitely stay there again!"
United States
Erin B.
The price is CA $245
CA $542 total
includes taxes & fees
Jul 9 - Jul 10
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
The price is CA $289
CA $743 total
includes taxes & fees
Jul 7 - Jul 8
Downtown Chicago Stay with Free In & Out Parking 5

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
9.8 out of 10, Exceptional, (17 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is CA $213
CA $262 total
includes taxes & fees
Jun 30 - Jul 1
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (51 reviews)
"Great stay"
United States
Steve T.
The price is CA $256
CA $531 total
includes taxes & fees
Jul 6 - Jul 7
LUXE 3 BR, 2 BA + Hot Tub

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.6 out of 10, Exceptional, (29 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
The price is CA $223
CA $485 total
includes taxes & fees
Jun 29 - Jun 30
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Countryside Hotel Reviews

Find out more about Countryside

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Countryside. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental near Countryside is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease 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 Millennium Park. In the larger area, you’ll find popular places like Soldier Field and Michigan Avenue.

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.