Photo by Monica Ferro

Countryside Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Countryside

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (410)
"The front desk staff were incredibly helpful, cheerfully assisted me with check-in and stored my extra bags early in the day when I went to work on the day u checked out. A service."
The price is ¥22,465
¥30,982 total
includes taxes & fees
May 27 - May 28
Sentral Michigan Avenue
Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very Good, (84)
"I loved having the whole space to ourselves. Felt the privacy of the entire building, more than a hotel. It was great. Would probably book again!"
The price is ¥13,816
¥16,219 total
includes taxes & fees
May 27 - May 28
Sonder Market Hall
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (300)
"It was a pleasant stay"
The price is ¥30,460
¥35,761 total
includes taxes & fees
May 28 - May 29
Sonder South Wabash
Save an average of 15% on thousands of hotels when you're signed in
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (238)
"Clean, friendly, spacious and at an excellent location."
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (208)
"Nice"
The price is ¥32,346
¥40,644 total
includes taxes & fees
May 27 - May 28
Level Chicago – Old Town
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (130)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is ¥29,035
¥34,085 total
includes taxes & fees
Jun 17 - Jun 18
Found Chicago powered by Sonder
Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (62)
" Cozy "
The price is ¥30,461
¥35,762 total
includes taxes & fees
May 28 - May 29
Sonder The Burnham
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (32)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (66)
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
Kasa River North Chicago
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, (102)
"The entire experience was fantastic. Clear instructions in how to get into the building and the apartment, fully stocked kitchen and extremely comfortable bed"
The price is ¥30,758
¥36,109 total
includes taxes & fees
May 28 - May 29
Sonder Jewelers Row
1 bedroom, premium bedding, pillowtop beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"Very nice property "
The price is ¥14,128
¥14,975 total
includes taxes & fees
May 27 - May 28
WoodSpring Suites Chicago Addison
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area | Smart TV, streaming services
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very Good, (67)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is ¥33,484
¥39,311 total
includes taxes & fees
Jun 23 - Jun 24
Sonder The Plymouth
3 bedrooms, WiFi, bed sheets
Your Home Away From Home
2.0 out of 10, (1)
"No me agradó"
The price is ¥23,549
¥27,114 total
includes taxes & fees
May 27 - May 28
Your Home Away From Home
Private kitchen | Fridge, microwave, oven, stovetop
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
"The house was beautifully decorated, well-equipped with all necessary amenities, and perfectly located close to Wrigley Field and the local establishments. If available, I highly recommend upgrading to the garage option for parking, especially during Cubs home games. This worked out perfectly for us. Justin was very helpful and responsive to my questions. We would definitely stay here again."
Wrigley/Southport Corridor Garden Oasis +parking!
Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
LakeHouse
Outdoor pool
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (198)
"This was an amazing place, in a great location, the view was unbelievable, and there was lots of things to do in the area our host, we’re great to work with, they had great insight, and information to share with us to make our stay even more enjoyable. we would definitely use their property again"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Smart TV, books
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (7)
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Don't see what you're looking for?
See all available properties in Countryside
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.

Other types of properties in Countryside you may be interested in

Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6807)
"No parking available "
The price is ¥23,332
¥27,393 total
includes taxes & fees
May 28 - May 29
Congress Plaza Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2904)
"Appreciated the easy of self serve check in and checkout. Did not have to stand in line. Only complaint is that the wait time for elevators is too long. Number iof elevators do not support number of guests"
The price is ¥22,222
¥26,088 total
includes taxes & fees
May 27 - May 28
River Hotel
Balcony
Eurostars Magnificent Mile
4.0 star property
8.4 out of 10, Very Good, (1955)
"Very Nice Hotel, In the heart of Chicago. Friendly and professional staff and the vallet guys are top notch not to mention cool. You are legit in walking distance of some if not all of what Chicago has to offer in terms of touristy type tings. "
The price is ¥28,258
¥33,174 total
includes taxes & fees
May 29 - May 30
Eurostars Magnificent Mile
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.

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?

Your Home Away From Home: Located near Countryside, this vacation home rental offers a fireplace, a spa tub, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a microwave to make your meal-planning easier.

What can I see and do in Countryside?

Explore the area and family-friendly sights such as Orland Park Sportsplex, 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.

Recent reviews of Countryside properties
Expedia verified reviews