Misty mountain valley

Hillside Holiday Rentals

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Our top choices for Hillside holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,188 reviews)
"Great location"
United States
JAVIER
The price is AU$337
includes taxes & fees
9 July - 10 July
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (492 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is AU$456
includes taxes & fees
30 June - 1 July
Level Chicago – Old Town

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.
The price is AU$1,117
includes taxes & fees
26 June - 27 June
River North Rooftop With In and Out Parking 1

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
The price is AU$781
includes taxes & fees
9 July - 10 July
River North Rooftop With In and Out Parking 5

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.4 out of 10, Exceptional, (30 reviews)
"A wonderful place to stay and everything was so perfect! Could not recommend staying here enough! "
United States
Cassidy L.
The price is AU$1,060
includes taxes & fees
8 July - 9 July
3BR Luxury Suite w/Gym and Balcony

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
United States
Emeline B.
The price is AU$1,359
includes taxes & fees
25 June - 26 June
ENVITAE Hotel, 4BR Luxury Modern Apartments

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (135 reviews)
"Perfect place to stay!"
United States
Anton
The price is AU$247
includes taxes & fees
17 June - 18 June
The Gem Museum Suites

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (23 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is AU$896
includes taxes & fees
28 June - 29 June
Modern West Loop Gem-City Views & Prime Location 6

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (20 reviews)
"Great place! The location is perfect. The apartment was comfortable for 5 people. Love the king beds in each room.It was clean and the staff was very helpful.Would definitely stay here again!"
United States
valerie h.
The price is AU$1,001
includes taxes & fees
5 July - 6 July
Spacious 4BR Central Apartment w/ Skyline Views

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
8.0 out of 10, Very good, (3 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.
The price is AU$485
includes taxes & fees
21 June - 22 June
Sunlit 1BR Apartment | Warm & Welcoming Space

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"We loved the location."
United States
Nicoll M.
The price is AU$566
includes taxes & fees
15 June - 16 June
LIVN Millennium Park Downtown Chicago Superior 2 BR

River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is AU$775
includes taxes & fees
12 July - 13 July
River North Private Balcony With In and Out Parking

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
Chic Studio in the Heart of the Gold Coast

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.2 out of 10, Wonderful, (12 reviews)
"The host was great at communicating and the apartment was very clean! "
United States
Hannah C.
The price is AU$473
includes taxes & fees
24 June - 25 June
West Loop Living – Bright 1BR

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is AU$937
includes taxes & fees
28 June - 29 June
River North Rooftop With In and Out Parking 6

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
The price is AU$416
includes taxes & fees
14 June - 15 June
LIVN West Loop Chicago Queen Superior Studio

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (61 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is AU$560
includes taxes & fees
9 July - 10 July
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is AU$848
includes taxes & fees
1 July - 2 July
River North Rooftop With In and Out Parking 3

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is AU$446
includes taxes & fees
30 June - 1 July
The Oak Park Loft

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.
The price is AU$436
includes taxes & fees
15 June - 16 June
Chicago-Themed 1BR in a Central Spot near Downtown
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 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, 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 favourite 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 depend 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 AU$142 per night. Entering your travel dates in the search wizard might find you 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Hillside is located in the city centre, and has a balcony, a BBQ 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 that 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 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.