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Top Holiday Rentals in Hillside

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (388)
"We really enjoyed our stay at Sentral. The property is conveniently located near Art Institute of Chicago, Millennium and Grant Park."
The price is £166
includes taxes & fees
28 May - 29 May
Sentral Michigan Avenue
Superior Studio, City View | Individually decorated, individually furnished, desk
Sonder Market Hall
3.5 star property
8.0 out of 10, Very good, (74)
"The property was nice, clean and fresh. The Studio was really nice and updated. "
The price is £109
includes taxes & fees
5 May - 6 May
Sonder Market Hall
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (294)
"Overall the stay was amazing. We will definitely be booking here again."
The price is £164
includes taxes & fees
28 May - 29 May
Sonder South Wabash
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Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (46)
"Only real issue was no late night (after 9) dining options. I got in later than expected & couldn't find even a fast food joint open after 9. Settled for 7-11 Pizza. "
The price is £182
includes taxes & fees
5 May - 6 May
Sonder The Burnham
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (123)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is £192
includes taxes & fees
29 May - 30 May
Found Chicago powered by Sonder
Smart TV
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (23)
"Beautiful, clean, new suites! Highly recommend! Easy to get to from public transport. The pull out sofa bed is not comfortable for those hoping to use it. But the main area bed was a dream! "
The price is £188
includes taxes & fees
6 May - 7 May
The Neighborhood Hotel-Little Italy
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (206)
"Nice"
The price is £204
includes taxes & fees
12 May - 13 May
Level Chicago – Old Town
Bar (on property)
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (97)
"The only real problem is train noise I was lucky that my unit was at the end of hallway so relatively far from train noise but they moved us for one night to another unit because of plumbing issue and as extremely noisy "
The price is £166
includes taxes & fees
28 May - 29 May
Sonder Jewelers Row
1 bedroom, premium bedding, pillow-top beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (183)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is £61
includes taxes & fees
7 May - 8 May
WoodSpring Suites Chicago Addison
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (65)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is £222
includes taxes & fees
22 May - 23 May
Sonder The Plymouth
3 bedrooms, WiFi, bed sheets
Your Home Away From Home
2.0 out of 10, (1)
The price is £141
includes taxes & fees
4 May - 5 May
Your Home Away From Home
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area | 42-inch Smart TV with digital channels, TV, streaming services
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (160)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.0 out of 10, Wonderful, (7)
"Great little home away from home. Definitely need to be painted and maintenance upgrades need to be addressed but other than that we had a great time"
The price is £145
includes taxes & fees
9 May - 10 May
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Full-sized fridge, oven, stovetop, dishwasher
Sonder The Opal
3.5 star property
8.0 out of 10, Very good, (12)
"Overall: A nice stay in a great part of town. Pros: Walking distance to almost everything downtown Chicago. Check-in is easy, but not the most intuitive instructions for the building codes. Spacious and clean room. Cons: The view. DO NOT let the pictures of the property deceive you… Unless you are on the top floor, the view is not very good. Also, says there’s rooftop access but no way to get to the roof (door locked). The walls are thin inside the apartment. Layout was a bit bizarre. Advert...
The price is £184
includes taxes & fees
28 May - 29 May
Sonder The Opal
Exterior
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (17)
"Great apartment! Perfect for 2 adults and 2 teens. Extremely close to Blue Line into Chicago. Easy drive to Wheaton (could have easily taken the Metra instead). Recommend Cuzzo pizza and Addis Cafe in Oak Park. One of us came down with a cold- grocery and drugstore nearby, and we spent the day playing cards and watching movies. Kitchenette was great for making our own (read: cheap) breakfasts each day. Thank you!"
Cozy modern unit w/ easy access to downtown Chi
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (6)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is £138
includes taxes & fees
22 May - 23 May
Ground Floor Studios in Chicago by 747 Lofts
40-inch flat-screen TV with digital channels, TV
Sonder Greektown
3.5 star property
8.8 out of 10, Excellent, (28)
"LOCATION was terrific - central and close to all our 'outings'. Downside was NOT being able to control the thermostat. And NO response to any of our efforts to contact the property manger(s)."
The price is £271
includes taxes & fees
29 May - 30 May
Sonder Greektown
Exterior
Chic Suite/Mins to L Train /Laundry/Free Parking
9.6 out of 10, Exceptional, (15)
"My wife and I spent a long weekend here. The apartment had plenty of room, was nicely decorated. The kitchen contained everything we needed to cook a full meal (which we did not). The bed is very comfortable. Ride service to downtown averaged $25. It was perfect."
The price is £153
includes taxes & fees
3 May - 4 May
Chic Suite/Mins to L Train /Laundry/Free Parking
Outdoor dining
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is £282
includes taxes & fees
5 May - 6 May
national historic home near downtown airports no parties no events
Don't see what you're looking for?
See all available properties in Hillside
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.

Hillside Holiday Rental Travel Info

Other types of properties in Hillside you may be interested in

Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6636)
"I loved my stay at the Congress Plaza Hotel! Check in was easy, especially since I got to check in at 12 noon, instead of 3PM. My room was very spacious and my king size bed was made up nicely and it was very comfortable too! There were plenty of towels in the pretty bathroom. The flatscreen TV was nice to watch. My room was very chilly at night because the HVAC registers are now set for warmer outdoor climates, but the lady at the front desk gave me a warm thick blanket to use. There are lots...
The price is £133
includes taxes & fees
13 May - 14 May
Congress Plaza Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2840)
"Loved the free water. Hotel staff (Pedro) was very friendly & helpful! The room was the perfect size for one person."
The price is £150
includes taxes & fees
12 May - 13 May
River Hotel
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2545)
"Its was a nice stay. "
The price is £143
includes taxes & fees
15 May - 16 May
Warwick Allerton - Chicago
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.

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, 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 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 £61 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?

Your Home Away From Home: This holiday home rental outside of Hillside offers a fireplace, 1 hot tub and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a microwave to make your meal-planning easier.

What can I see and do in Hillside?

Enjoy the area's cultural attractions such as Art Institute of Chicago, or get outdoors into nature at a spot like Grant Park. Other popular places to visit in the area include Wrigley Field and Navy Pier.

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.

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