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Hillside Vacation Rentals

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Vacation Rentals in Hillside

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (417)
"Great location for museum campus area!!!"
The price is ¥29,575
¥39,336 total
includes taxes & fees
Jun 16 - Jun 17
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very Good, (89)
"Really pleased with my stay at the Market Hall. The process was extremely easy to reserve and access the room. The room was better than expected. I would definitely stay here again. Thanks Sonder!! "
The price is ¥21,793
¥25,585 total
includes taxes & fees
Jun 16 - Jun 17
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (302)
"Everything was great!"
The price is ¥30,502
¥35,808 total
includes taxes & fees
Jun 5 - Jun 6
Sonder South Wabash
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Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (244)
"Host was easily accessible. We had a relaxing stay and the apartment is very comfortable as well as clean. Definitely will stay here again."
The price is ¥31,488
¥52,882 total
includes taxes & fees
Jun 4 - Jun 5
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (209)
"Nice"
The price is ¥60,961
¥74,242 total
includes taxes & fees
Jun 6 - Jun 7
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (130)
"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 ¥29,598
¥34,747 total
includes taxes & fees
Jun 27 - Jun 28
Found Chicago powered by Sonder
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (66)
" Cozy "
The price is ¥35,999
¥42,263 total
includes taxes & fees
Jun 12 - Jun 13
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (33)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (67)
"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 ¥37,380
¥43,884 total
includes taxes & fees
Jun 2 - Jun 3
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, (104)
"Loved it "
The price is ¥38,175
¥44,817 total
includes taxes & fees
Jun 18 - Jun 19
Sonder Jewelers Row
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (185)
"Very nice property "
The price is ¥14,149
¥14,998 total
includes taxes & fees
Jun 4 - Jun 5
WoodSpring Suites Chicago Addison
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"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 ¥33,538
¥39,374 total
includes taxes & fees
Jun 19 - Jun 20
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
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 ¥28,375
¥35,784 total
includes taxes & fees
Jun 3 - Jun 4
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
"The house was beautifully decorated, well-equipped with all necessary amenities, and perfectly located close to Wrigley Field and the local establishments. If available, I highly recommend upgrading to the garage option for parking, especially during Cubs home games. This worked out perfectly for us. Justin was very helpful and responsive to my questions. We would definitely stay here again."
Wrigley/Southport Corridor Garden Oasis +parking!
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
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
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (7)
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
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.

Other types of properties in Hillside you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6813)
"Be aware there is only Analog TV in the room"
The price is ¥27,913
¥32,769 total
includes taxes & fees
Jun 5 - Jun 6
Congress Plaza Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2921)
"The facility was beautiful. The staff was extremely friendly and helpful. The views of the city were phenomenal. "
The price is ¥26,807
¥31,472 total
includes taxes & fees
Jun 30 - Jul 1
River Hotel
Eurostars Magnificent Mile
4.0 star property
8.4 out of 10, Very Good, (1988)
"convenient location in the area "
The price is ¥26,799
¥31,461 total
includes taxes & fees
Jun 30 - Jul 1
Eurostars Magnificent Mile
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.

Search for holiday rentals in Hillside on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillside using one of the methods below:

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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 are some of the best vacation rentals that Hillside has to offer?

Your Home Away From Home: This vacation home rental outside of Hillside offers a fireplace, a spa 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 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.

Recent reviews of Hillside properties
Expedia verified reviews