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Hillside Holiday Rentals

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Holiday Rentals in Hillside

Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (172)
"This place has everything for a multi-night stay."
United States
Dane
The price is AU$464
includes taxes & fees
27 Oct - 28 Oct
Kasa River North Chicago
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (961)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is AU$289
includes taxes & fees
11 Nov - 12 Nov
Sentral Michigan Avenue
2-bedroom apartment just 2 minutes drive to Wrigley Field
2.0 star property
9.6 out of 10, Exceptional, (47)
"Great place to stay when you’re in town for the Cubbies! "
United States
Eric
The price is AU$508
includes taxes & fees
22 Oct - 23 Oct
2-bedroom apartment just 2 minutes drive to Wrigley Field
Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
The price is AU$765
includes taxes & fees
22 Oct - 23 Oct
Enamored in Elmhurst
Historic Oak Park Home
2.0 star property
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is AU$415
includes taxes & fees
10 Nov - 11 Nov
Historic Oak Park Home
The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5)
"This apartment was is so cute! Hosts were awesome."
United States
Cindy
The price is AU$382
includes taxes & fees
16 Nov - 17 Nov
The Oak Park Loft
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (369)
"Friendly staff and great amenities "
United States
Bryan
The price is AU$357
includes taxes & fees
3 Nov - 4 Nov
Level Chicago – Old Town
The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (92)
"Super nice hotel and staff "
United States
EMILY
The price is AU$318
includes taxes & fees
29 Oct - 30 Oct
The Gem Museum Suites
Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (24)
"The entirety of my experience was excellent. Thank you!"
United States
Julian
The price is AU$189
includes taxes & fees
22 Oct - 23 Oct
Wrigleyville Suites
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
3.5 star property
8.6 out of 10, Excellent, (691)
"Location was nice."
United States
Juliet
The price is AU$228
includes taxes & fees
3 Nov - 4 Nov
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Haus Of Hues: MDRN Bright Peaceful Private Apt
2.0 star property
9.4 out of 10, Exceptional, (14)
"Nice quiet part of town with easy access to different parts of the city. Great communication before and during our stay. Definitely enjoyed our time. "
United States
Ali A.
The price is AU$695
includes taxes & fees
22 Oct - 23 Oct
Haus Of Hues: MDRN Bright Peaceful Private Apt
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (20)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago by 747 Lofts
4BR Corporate Suite Central and Modern
2.0 star property
10.0 out of 10, Exceptional, (4)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is AU$524
includes taxes & fees
22 Oct - 23 Oct
4BR Corporate Suite Central and Modern
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
10.0 out of 10, Exceptional, (34)
"Lovely property, well equipped and a responsive host! Would definitely recommend."
United States
Bryan S.
The price is AU$942
includes taxes & fees
22 Oct - 23 Oct
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Chicago luxury home suites
2.0 star property
The price is AU$1,757
includes taxes & fees
30 Oct - 31 Oct
Chicago luxury home suites
At Home in Oak Park
3.5 star property
9.4 out of 10, Exceptional, (8)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
United States
Kathryn
The price is AU$408
includes taxes & fees
11 Nov - 12 Nov
At Home in Oak Park
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
9.6 out of 10, Exceptional, (24)
"The property was great. Clean, charming, and full of accommodations. Check in/out was really simple if you need a quick place to crash, but has everything you need for a longer stay. The best part was the communication with the host though. Very easy to get in touch with, very detailed in answering questions, and was understanding when discussing damage found from a previous guest. Overall would stay again. "
United States
Alex P.
The price is AU$715
includes taxes & fees
22 Oct - 23 Oct
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Chic Urban Retreat Near Wrigley Field w/Parking
10.0 out of 10, Exceptional, (40)
"The property was amazing, clean and well organized. Parking was a breeze and check in was easy. Would recommend this place to anyone looking to stay in the area."
United States
Todd
The price is AU$697
includes taxes & fees
29 Oct - 30 Oct
Chic Urban Retreat Near Wrigley Field w/Parking
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (51)
"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"
United States
Mary
The price is AU$478
includes taxes & fees
27 Oct - 28 Oct
✽ Charming Cottage ✽ close to College/Town/Station
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (242)
"Great stay. "
United States
Teresa
The price is AU$243
includes taxes & fees
9 Nov - 10 Nov
Sonder by Marriott Bonvoy The Burnham Apartments Loop
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$189 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.