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Hillside Holiday Rentals

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Holiday Rentals in Hillside

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (928)
"The staff was extremely helpful and the rooms are clean with a beautiful view of downtown and the lake. I will definitely stay here again. "
The price is NZ$443
includes taxes & fees
5 Oct - 6 Oct
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (529)
"Very great place to stay!"
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (356)
"Real nice place 5 stars ill be back."
Level Chicago – Old Town

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (662)
"Dangerous area at times… but not always bad. And a quick walk to the safe areas for sure!!! I would definitely stay here again."
The price is NZ$376
includes taxes & fees
9 Oct - 10 Oct
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very good, (366)
"Great stay!"
The price is NZ$273
includes taxes & fees
19 Oct - 20 Oct
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (353)
"It was a really nice and secure property. "
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (230)
"Great location and lovely amenities. "
The price is NZ$376
includes taxes & fees
26 Oct - 27 Oct
Sonder by Marriott Bonvoy The Burnham Apartments Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (202)
"This place was perfect "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (50)
"Place was in a great location close to good restaurants "
The price is NZ$341
includes taxes & fees
19 Oct - 20 Oct
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (169)
"This place has everything for a multi-night stay."
Kasa River North Chicago

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
The price is NZ$414
includes taxes & fees
5 Oct - 6 Oct
The Gem Museum Suites

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
Wrigleyville Suites

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (180)
"Great location!!!"
The price is NZ$361
includes taxes & fees
1 Oct - 2 Oct
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (138)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is NZ$299
includes taxes & fees
26 Oct - 27 Oct
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
Art Villa

Clean & Equipped 1BR Apt

9.4 out of 10, Exceptional, (24)
"Good experience. Would stay there again "
The price is NZ$320
includes taxes & fees
1 Oct - 2 Oct
Clean & Equipped 1BR Apt

Cozy, Fully Set-Up 1BR Space

9.2 out of 10, Wonderful, (22)
"We are very happy with our stay! Big comfy bed with good bed lining, a proper kitchen, a spacious bathroom, and everything was clean and nice. This place has everything you need! And communication with the host was excellent. Truly highly recommend!"
The price is NZ$322
includes taxes & fees
1 Oct - 2 Oct
Cozy, Fully Set-Up 1BR Space

Charming 2BR in Vibrant Lakeview

9.4 out of 10, Exceptional, (18)
"Overall, this property is really quite great. We wanted someplace close to our daughter in Wrigleyville, and we found the location to be excellent. The apartment itself is located in a vintage apartment complex consisting of four buildings around a center courtyard. The entire complex is gated and locked and felt very secure. It is set back off the street and because of that it is not terribly loud. The unit is attractively renovated and is well represented by the images shown here. The kitchen...
The price is NZ$366
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR in Vibrant Lakeview

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is NZ$386
includes taxes & fees
30 Sept - 1 Oct
Stylish 1BR in West Loop

Lakeview 2BR Apartment

9.4 out of 10, Exceptional, (15)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
The price is NZ$348
includes taxes & fees
1 Oct - 2 Oct
Lakeview 2BR 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 Hillside Hotel Reviews

Find out more about Hillside

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$273 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?

2BR Traveler's Favorite, Modern and Clean: This holiday home rental outside of Hillside offers a garden, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.