Hillside Vacation Rentals

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Our top choices for Hillside vacation rentals

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
$204 nightly
The price is $228
Jun 3 - Jun 4
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
$186 nightly
The price is $209
Jun 8 - Jun 9
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast

River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
$436 nightly
The price is $503
Jun 10 - Jun 11
Total with taxes and fees
River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
$489 nightly
The price is $568
Jun 10 - Jun 11
Total with taxes and fees
River North Rooftop With In and Out Parking 1

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (11 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
$285 nightly
The price is $324
Jun 4 - Jun 5
Total with taxes and fees
West Loop Living – Bright 1BR

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,179 reviews)
"Great location"
United States
Karen
$225 nightly
The price is $264
Jul 2 - Jul 3
Total with taxes and fees
Sentral Michigan Avenue

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
$243 nightly
The price is $274
Jun 8 - Jun 9
Total with taxes and fees
Chicago-Themed 1BR in a Central Spot near Downtown

Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (63 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
$181 nightly
The price is $207
Jun 24 - Jun 25
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.4 out of 10, Exceptional, (8 reviews)
"Excellent location, very clean & comfortable. West Loop is an awesome area to stay in Chicago. Seamless check in process."
United States
Dean R.
$515 nightly
The price is $565
Jun 28 - Jun 29
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 2

Bright Garden Studio

Bright Garden Studio
South Evanston
8.2 out of 10, Very Good, (35 reviews)
"Easy access. Nice location. Available shrot notice."
United States
Drew H.
$232 nightly
The price is $264
Jun 3 - Jun 4
Total with taxes and fees
Bright Garden Studio

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (78 reviews)
"Great stay i loved it"
United States
Cedes W.
$145 nightly
The price is $178
Jun 16 - Jun 17
Total with taxes and fees
Cozy studio in Andersonville Chicago

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.2 out of 10, Wonderful, (7 reviews)
"It was really a great place. Bb oo"
United States
Kate S.
$174 nightly
The price is $195
Jun 9 - Jun 10
Total with taxes and fees
Trendy & Comfy Studio Unit

Homey Hyde Park Studio Near UChicago

Homey Hyde Park Studio Near UChicago
Hyde Park
9.6 out of 10, Exceptional, (5 reviews)
"Location was just perfect!"
United States
Meg D.
$164 nightly
The price is $183
Jun 3 - Jun 4
Total with taxes and fees
Homey Hyde Park Studio Near UChicago

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
10.0 out of 10, Exceptional, (11 reviews)
$876 nightly
The price is $1,081
Jun 25 - Jun 26
Total with taxes and fees
ENVITAE Hotel, 4BR Luxury Modern Apartments

Sunlit Studio with City Charm

Sunlit Studio with City Charm
Rogers Park
8.4 out of 10, Very Good, (13 reviews)
"Host was extremely welcoming and accommodating. They went out of their way to assure me that they were but a call away if there was anything we needed."
United States
Renee W.
$176 nightly
The price is $197
Jun 8 - Jun 9
Total with taxes and fees
Sunlit Studio with City Charm

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (49 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
$209 nightly
The price is $237
Jun 9 - Jun 10
Total with taxes and fees
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (484 reviews)
"Staff was amazing and the apartment building was phenomenally clean!"
United States
Seke
$262 nightly
The price is $308
Jun 30 - Jul 1
Total with taxes and fees
Level Chicago – Old Town

Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
9.4 out of 10, Exceptional, (10 reviews)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
$197 nightly
The price is $217
Jun 3 - Jun 4
Total with taxes and fees
Comfortable 2BR Chicago Apt

Cozy 1BR in Walkable Area

Cozy 1BR in Walkable Area
Lincoln Square
9.8 out of 10, Exceptional, (14 reviews)
"Spotless, great location, would definitely stay again!"
United States
Debbie G.
$171 nightly
The price is $190
Jun 9 - Jun 10
Total with taxes and fees
Cozy 1BR in Walkable Area

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (30 reviews)
"great stay for the guys."
United States
Louise D.
$169 nightly
The price is $180
Jun 3 - Jun 4
Total with taxes and fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
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

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 $121 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 are some of the best vacation rentals that Hillside has to offer?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This vacation home rental outside of Hillside is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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 Wrigley Field and Michigan Avenue.

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.