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Hillside Vacation Rentals

Vacation Rentals in Hillside

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (429)
"Nice place very nice front desk"
The price is $170
$229 total
includes taxes & fees
3 Jul - 4 Jul
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very Good, (95)
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is $100
$117 total
includes taxes & fees
30 Jun - 1 Jul
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (312)
"Pretty nice but the outlet and few other items not functioning "
The price is $189
$222 total
includes taxes & fees
2 Jul - 3 Jul
Sonder South Wabash
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Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (250)
"Had some difficulty finding a USB charging port. It was located under the kitchen counter-top."
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (214)
"The staff here is amazing and so helpful. Loved my stay here. "
The price is $244
$303 total
includes taxes & fees
30 Jun - 1 Jul
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (132)
"I loved my stay at Found Chicago! The logistical communication was easy to understand and implement, and I liked that it was contactless. It was nice to use my PIN code for room entrance instead of keeping track of a key. The WiFi was sufficient for remote meetings on my laptop. And all of the amenities (lobby access, luggage locker, and printer) were convenient and easy to use. I highly recommend this hotel, and I'll plan to stay here again. "
The price is $189
$222 total
includes taxes & fees
30 Jun - 1 Jul
Found Chicago powered by Sonder
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (78)
"I like the hotel, I did not realize there was no cleaning services or fresh towels. After 4 days the room needed some freshing and clean wash rags and towels. There was a washing machine but doing laundry on vacation is not for me."
The price is $235
$276 total
includes taxes & fees
30 Jun - 1 Jul
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (34)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (188)
"Very nice property "
The price is $90
$95 total
includes taxes & fees
9 Jun - 10 Jun
WoodSpring Suites Chicago Addison
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (68)
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
The price is $359
$421 total
includes taxes & fees
12 Jun - 13 Jun
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, (107)
"Loved it "
The price is $191
$224 total
includes taxes & fees
7 Jul - 8 Jul
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (162)
"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
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very Good, (68)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is $218
$256 total
includes taxes & fees
2 Jul - 3 Jul
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (107)
"The place was nice and clean but missing some basic items such as floor mats and decent pans, otherwise our stay was good. It was near all the places we need to go"
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is $152
$195 total
includes taxes & fees
9 Jun - 10 Jun
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (40)
"Well renovated, nice bathroom."
Wrigley/Southport Corridor Garden Oasis +parking!
LakeHouse
10.0 out of 10, Exceptional, (7)
"Great"
LakeHouse
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (200)
"Everything was perfect. Doormen so nice & helpful. The condo is warm & welcoming. Very easy to feel at home."
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Sonder The Opal
3.5 star property
8.2 out of 10, Very Good, (15)
"I like that was contactless and easy to access. "
The price is $233
$274 total
includes taxes & fees
1 Jul - 2 Jul
Sonder The Opal
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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 Vacation Rental Travel Info

Other types of properties in Hillside you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6870)
"Nice place."
The price is $164
$193 total
includes taxes & fees
29 Jun - 30 Jun
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very Good, (2376)
"Very good location "
The price is $199
$234 total
includes taxes & fees
17 Jun - 18 Jun
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2962)
"Excellent property "
The price is $145
$171 total
includes taxes & fees
8 Jul - 9 Jul
River Hotel
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillside vacation 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 low season months. For more hustle and bustle, you may prefer to visit Hillside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Hillside rentals

At Expedia, we put the best Hillside vacation 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 vacation.

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 vacation rental in Hillside?

Yes, you can find vacation rentals near popular sights in Hillside, or you can choose a secluded option if you're looking for relaxation. Visitors like the top-notch restaurants and forests in Hillside. Allow some time to check out the shops during your trip.

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 vacation rentals like in Hillside?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Hillside. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.

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