Hillside Holiday Rentals

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Our top choices for Hillside holiday rentals

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,104 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is AU$236
includes taxes & fees
19 Mar - 20 Mar
Sentral Michigan Avenue
9.6 out of 10, Exceptional, (4 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 AU$622
includes taxes & fees
18 Mar - 19 Mar
River North Rooftop With In and Out Parking 3

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (441 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (186 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Apartment in Downtown Chicago

Modern Comfort: 1BR Unit w/ Laundry
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is AU$326
includes taxes & fees
15 Mar - 16 Mar
Modern Comfort: 1BR Unit w/ Laundry

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
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 AU$326
includes taxes & fees
15 Mar - 16 Mar
Sun-Drenched 1BR Apartment
The price is AU$1,067
includes taxes & fees
16 Mar - 17 Mar
Modern 4BR Gold Coast Duplex w/ Jacuzzi & Balcony
10.0 out of 10, Exceptional, (15 reviews)
"Great place"
United States
Daniel L.
The price is AU$683
includes taxes & fees
29 Mar - 30 Mar
Modern West Loop Gem-City Views & Prime Location 6

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (8 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is AU$326
includes taxes & fees
15 Mar - 16 Mar
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

Chic Studio in the Heart of the Gold Coast
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is AU$335
includes taxes & fees
24 Mar - 25 Mar
Chic Studio in the Heart of the Gold Coast
8.6 out of 10, Excellent, (26 reviews)
"Amazing location. Completely thrilled with our choice of this beautiful place. Thank you!"
United States
Emily M.
The price is AU$731
includes taxes & fees
16 Mar - 17 Mar
Modern|Aesthetic|2BR|Evanston|Next to Beach
9.8 out of 10, Exceptional, (18 reviews)
"Plenty of space for my family and loved the onsite free parking, that was helpful because we drove everywhere, just a 30 min drive into the heart of the city"
United States
Jessica T.
The price is AU$951
includes taxes & fees
16 Mar - 17 Mar
Chic 3bed 2bath Home with free parking close to United Center

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AU$331
includes taxes & fees
17 Mar - 18 Mar
1BR Modern Luxe Apt with In-Unit Laundry
9.4 out of 10, Exceptional, (22 reviews)
"Everything was excellent. Highly recommended!!!"
United States
Donald S.
The price is AU$1,312
includes taxes & fees
12 Mar - 13 Mar
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
The price is AU$972
includes taxes & fees
30 Mar - 31 Mar
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Holiday Home in Oak Park

A quiet stay while you are away
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is AU$344
includes taxes & fees
18 Mar - 19 Mar
A quiet stay while you are away
10.0 out of 10, Exceptional, (5 reviews)
"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.
The price is AU$652
includes taxes & fees
30 Mar - 31 Mar
Modern West Loop Gem-City Views & Prime Location 3

Apartment in Near West Side

Your Perfect 2BR Home
8.4 out of 10, Very good, (15 reviews)
"Great location! "
United States
Kourtney K.
The price is AU$355
includes taxes & fees
16 Mar - 17 Mar
Your Perfect 2BR Home

Holiday Home in Oak Park

Oak Park Victorian by FLW Studio
10.0 out of 10, Exceptional, (29 reviews)
"Finding a good 3 br or 4 br option in and around OP / RF is challenging and if this one is available, jump on it. Functional plan, easy parking, great location and responsive owners. "
United States
Lawrence P.
The price is AU$770
includes taxes & fees
18 Mar - 19 Mar
Oak Park Victorian by FLW Studio

Aparthotel in West Town

Cabin 105 by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (1 review)
The price is AU$289
includes taxes & fees
15 Mar - 16 Mar
Cabin 105 by 747 Lofts
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 Hillside Hotel Reviews

Find out more about Hillside

Everything you need to know about Hillside 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 Hillside holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Hillside holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Hillside holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillside. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillside 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 Hillside holiday rentals we have selected for you start as low as AU$152 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hillside rentals

At Expedia, we put the best Hillside 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 Hillside 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 Hillside 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 Hillside. 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 a holiday rental in Hillside?

Yes, there are holiday rentals close to the most popular sights in Hillside, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and forests in Hillside. Allow some time to check out the shops during your trip.

What are some of the best holiday rentals that Hillside has to offer?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This holiday home rental outside of Hillside is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Hillside?

Enjoy the area's cultural attractions such as Drury Lane Theater, or get outdoors into nature at a spot like Millennium Park. Other popular places to visit in the area include Wrigley Field and Michigan Avenue.

What are holiday rentals like in Hillside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Hillside. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.