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Countryside Vacation Rentals

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Vacation Rentals in Countryside

Our top choices for Countryside vacation rentals

Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (926)
"The staff was extremely helpful and the rooms are clean with a beautiful view of downtown and the lake. I will definitely stay here again. "
The price is ￥26,222
￥35,113 total
includes taxes & fees
Sep 25 - Sep 26
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (529)
"Very great place to stay!"
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (356)
"Real nice place 5 stars ill be back."
Level Chicago – Old Town
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (662)
"Dangerous area at times… but not always bad. And a quick walk to the safe areas for sure!!! I would definitely stay here again."
The price is ￥24,968
￥29,310 total
includes taxes & fees
Oct 7 - Oct 8
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very Good, (364)
"Great stay!"
The price is ￥19,949
￥23,420 total
includes taxes & fees
Oct 19 - Oct 20
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (353)
"It was a really nice and secure property. "
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (230)
"Great location and lovely amenities. "
The price is ￥28,732
￥33,728 total
includes taxes & fees
Oct 23 - Oct 24
Sonder by Marriott Bonvoy The Burnham Apartments Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (202)
"This place was perfect "
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very Good, (49)
"Place was in a great location close to good restaurants "
The price is ￥24,968
￥29,310 total
includes taxes & fees
Oct 19 - Oct 20
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business center

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (169)
"This place has everything for a multi-night stay."
Kasa River North Chicago
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
Wrigleyville Suites
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (61)
"Good "
The price is ￥12,487
￥14,106 total
includes taxes & fees
Sep 25 - Sep 26
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (180)
"Great location!!!"
The price is ￥26,422
￥31,016 total
includes taxes & fees
Oct 1 - Oct 2
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (138)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is ￥21,832
￥25,628 total
includes taxes & fees
Oct 21 - Oct 22
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Art Villa
Design Townhome, 3 Bedrooms, Kitchen, City View | Living area | 55-inch Smart TV with digital channels, fireplace, Netflix

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
Art Villa
Clean & Equipped 1BR Apt
1 bedroom, iron/ironing board, WiFi, bed sheets

Clean & Equipped 1BR Apt

9.4 out of 10, Exceptional, (23)
"Good experience. Would stay there again "
The price is ￥11,661
￥27,635 total
includes taxes & fees
Oct 1 - Oct 2
Clean & Equipped 1BR Apt
Cozy, Fully Set-Up 1BR Space
Fridge, microwave, oven, stovetop

Cozy, Fully Set-Up 1BR Space

9.2 out of 10, Wonderful, (22)
"We are very happy with our stay! Big comfy bed with good bed lining, a proper kitchen, a spacious bathroom, and everything was clean and nice. This place has everything you need! And communication with the host was excellent. Truly highly recommend!"
The price is ￥11,661
￥27,635 total
includes taxes & fees
Oct 1 - Oct 2
Cozy, Fully Set-Up 1BR Space
Charming 2BR in Vibrant Lakeview
2 bedrooms, iron/ironing board, travel crib, WiFi

Charming 2BR in Vibrant Lakeview

9.4 out of 10, Exceptional, (18)
"Overall, this property is really quite great. We wanted someplace close to our daughter in Wrigleyville, and we found the location to be excellent. The apartment itself is located in a vintage apartment complex consisting of four buildings around a center courtyard. The entire complex is gated and locked and felt very secure. It is set back off the street and because of that it is not terribly loud. The unit is attractively renovated and is well represented by the images shown here. The kitchen...
The price is ￥12,990
￥31,406 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2BR in Vibrant Lakeview
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is ￥16,532
￥33,342 total
includes taxes & fees
Sep 30 - Oct 1
Stylish 1BR in West Loop
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop

Lakeview 2BR Apartment

9.4 out of 10, Exceptional, (13)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
The price is ￥11,661
￥29,850 total
includes taxes & fees
Oct 1 - Oct 2
Lakeview 2BR Apartment
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

10/10 Excellent
"Staff was very helpful. Smooth check in and out!"
Melissa 3-night trip
Posted 12 hours ago
Congress Plaza Hotel

Find out more about Countryside

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:

  • View our selection of featured holiday rentals in Countryside
  • Use the map to find apartments and other holiday homes in the Countryside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Countryside while they last

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?

2BR Traveler's Favorite, Modern and Clean: This vacation home rental near Countryside offers a garden, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Countryside?

Explore the area and family-friendly sights such as Parkway Bank Park Entertainment District, or get out into nature at a spot like Millennium Park. In the larger area, you’ll find popular places like Michigan Avenue and Navy Pier.

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.