Hillside Holiday Rentals

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Our top choices for Hillside holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,079 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is NZ$262
includes taxes & fees
22 Feb - 23 Feb
Sentral Michigan Avenue

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (427 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is NZ$425
includes taxes & fees
16 Feb - 17 Feb
The Oak Park Loft

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
Chicago Third Floor Studio by 747 Lofts

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Wanted a house in oak park and this was such a pleasant, comfortable and convenient place. Really comfortable beds too. Even a lovely piano. "
United States
judith
The price is NZ$445
includes taxes & fees
2 Mar - 3 Mar
Historic Oak Park Home

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (29 reviews)
"Nice place "
United States
Barry
The price is NZ$231
includes taxes & fees
16 Feb - 17 Feb
Wrigleyville Suites

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (104 reviews)
"This is a fantastic hotel with super friendly staff"
United States
German
The price is NZ$327
includes taxes & fees
16 Feb - 17 Feb
The Gem Museum Suites

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Absolutely awesome "
United States
Erik
The price is NZ$465
includes taxes & fees
2 Mar - 3 Mar
Historic Oak Park Residence

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.4 out of 10, Exceptional, (9 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is NZ$435
includes taxes & fees
2 Mar - 3 Mar
At Home in Oak Park

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (17 reviews)
"Loved the space and location "
United States
Caroline
River West, Third Floor Chicago 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 favorite 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 depends 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 NZ$215 per night. Entering your travel dates in the search wizard you might find 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?

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!: This holiday home rental outside of Hillside is on a lake, and equipped with 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 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 United Center and Wrigley Field.

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.