A lush green valley with a winding road, steep mountains, and a misty atmosphere.

Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Hillside vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,225 reviews)
"Great location. Great views of the lake. Great pool, lounge area. Great restaurants right next door."
United States
Patricia
The price is ￥27,396
￥36,969 total
includes taxes & fees
Aug 24 - Aug 25
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (507 reviews)
"Perfect location"
United States
Diana
The price is ￥44,830
￥56,668 total
includes taxes & fees
Aug 24 - Aug 25
Level Chicago – Old Town
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ￥31,056
￥53,748 total
includes taxes & fees
Jul 27 - Jul 28
The Oak Park Loft
Breakfast, lunch and dinner served

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (168 reviews)
"Beautiful hotel, gardened a plus! Located in very nice neighborhood, near the train, breakfast was vey good well. Would stay there again"
United States
Jacob
The price is ￥24,073
￥27,559 total
includes taxes & fees
Aug 20 - Aug 21
The Gem Museum Suites
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is ￥35,159
￥58,445 total
includes taxes & fees
Aug 17 - Aug 18
Historic Oak Park Home
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.8 out of 10, Excellent, (45 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is ￥31,268
￥36,705 total
includes taxes & fees
Jul 27 - Jul 28
Wrigleyville Suites
Apartment, Private Bathroom | Lounge

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is ￥39,286
￥63,086 total
includes taxes & fees
Jul 26 - Jul 27
At Home in Oak Park
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

River Hotel

River Hotel

10/10 Excellent
"Loved everything about this stay EXCEPT the broken elevator. Staff was wonderful, room was quiet, water was hot! And yes, I would stay again!✨"
Andrea 4-night trip
Posted 5 hours ago
River Hotel

Find out more about Hillside

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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Look no further and take a look at our great range of rental properties in Hillside!

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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental outside of Hillside is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 United Center and Wrigley Field.

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.