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Our top choices for Countryside holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,159 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is £153
includes taxes & fees
25 May - 26 May
Sentral Michigan Avenue

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is £192
includes taxes & fees
20 May - 21 May
Modern Comfort: 1BR Unit w/ Laundry

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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 £282
includes taxes & fees
21 May - 22 May
Sunlit 1BR Apartment | Warm & Welcoming Space

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (22 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is £438
includes taxes & fees
13 May - 14 May
Modern West Loop Gem-City Views & Prime Location 6

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (752 reviews)
"Great location"
United States
Alex
The price is £199
includes taxes & fees
13 May - 14 May
Kasa Magnificent Mile Chicago

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, (5 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 £439
includes taxes & fees
27 May - 28 May
River North Rooftop With In and Out Parking 3

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is £229
includes taxes & fees
19 May - 20 May
West Loop Living – Bright 1BR

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)
"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
The price is £167
includes taxes & fees
13 May - 14 May
Chic Studio in the Heart of the Gold Coast

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.8 out of 10, Good, (7 reviews)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
United States
Leah W.
The price is £148
includes taxes & fees
26 May - 27 May
Uptown Studio Gem Sum

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is £405
includes taxes & fees
18 May - 19 May
LIVN Millennium Park Downtown Chicago 2BR

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is £165
includes taxes & fees
2 Jun - 3 Jun
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is £299
includes taxes & fees
13 May - 14 May
Spacious 4BR Central Apartment w/ Skyline Views

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is £532
includes taxes & fees
15 May - 16 May
LIVN West Loop Chicago King 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, (72 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is £263
includes taxes & fees
20 May - 21 May
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, (474 reviews)
"Love the amenities. Great location too"
United States
Paul
The price is £207
includes taxes & fees
26 May - 27 May
Level Chicago – Old Town

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.0 out of 10, Wonderful, (15 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 £147
includes taxes & fees
13 May - 14 May
Charming Sunlit 1BR Apartment

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (24 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is £223
includes taxes & fees
18 May - 19 May
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

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 location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is £391
includes taxes & fees
18 May - 19 May
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (192 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is £271
includes taxes & fees
27 May - 28 May
Kasa River North Chicago

Homey 1BR Space Apartment

Homey 1BR Space Apartment
Lincoln Square
9.4 out of 10, Exceptional, (18 reviews)
"Love the location right in Lincoln Square. "
United States
Ticia B.
The price is £162
includes taxes & fees
19 May - 20 May
Homey 1BR Space 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

Find out more about Countryside

Everything you need to know about Countryside holiday rentals

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

Countryside holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Countryside holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Countryside holiday rentals we have selected for you start as low as £83 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Countryside rentals

At Expedia, we put the best Countryside holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Countryside?

Yes, there are holiday rentals close to the most popular sights in Countryside, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Countryside has to offer?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This holiday home rental outside of Countryside is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 Grant Park. In the wider area, you’ll find popular places such as Navy Pier and Wrigley Field.

What are holiday rentals like in Countryside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Countryside. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for small groups.