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Hillside holiday rentals

We found 551 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Scroll through and select from holiday rentals in Hillside to find one that's perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include parking and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The relaxing area of Hillside awaits your stay

Enjoy the live music and other features of Hillside. Travellers especially like the shopping, restaurants and forests in this relaxing and welcoming city. Wrigley Field and Grant Park are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Hillside

Are you looking for attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that Hillside has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Galloping Ghost (4.9 mi / 7.8 km)
  • The Dome at the Parkway Bank Sports Complex (7.3 mi / 11.7 km)
  • TopGolf Chicago (8.8 mi / 14.2 km)
  • LEGOLAND® Discovery Center (13.1 mi / 21 km)
  • Lincoln Park Zoo (14.2 mi / 22.8 km)
  • Cog Hill Golf & Country Club (14.4 mi / 23.2 km)

Exploring the natural landscape of Hillside

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Hillside is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Grant Park (14.5 mi / 23.4 km)
  • Millennium Park (14.4 mi / 23.2 km)
  • Norridge Park District (7.5 mi / 12 km)
  • Morton Arboretum (8.6 mi / 13.9 km)
  • Portage Park (8.9 mi / 14.3 km)
  • Garfield Park (9.5 mi / 15.3 km)

Travelling to and around Hillside

The nearest airport is in Chicago O'Hare International Airport (ORD), located 6.9 mi (11 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Chicago Midway Airport (MDW), which is 10.4 mi (16.7 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Hillside?

The most desirable types of holiday homes in Hillside are apartments. Want something different? Vrbo has numerous options to match our guests' needs, so you'll see properties in lots of sizes and shapes. The perfect fit is ready and waiting for you — get hold of yours today.

How much does it cost to rent a holiday home in Hillside?

The average price for a holiday home in Hillside is determined by several factors, including length of stay, season and property type. Whether you'd like a sprawling villa with space for extended family or a comfy cabin ideal for just you and the kids, just enter your travel dates to discover stays with unbeatable value.

How much does it cost to rent a beach house in Hillside?

When you travel and the style and size of the property will influence how much you'll pay for your beachside escape. Type in your Hillside travel dates to view your options on Vrbo. Can't live without a hot tub? Use the filters to pick the features and amenities you want.

What are the top attractions for families in Hillside?

Keeping the kids entertained during your stay in Hillside is a breeze with these cool family-friendly attractions:

  • Brookfield Zoo
  • Parkway Bank Park Entertainment District
  • Galloping Ghost

How old do you have to be to rent a holiday home in Hillside?

You'll need to check with the Hillside holiday home you're looking at on Vrbo as the age limit differs. However, it's generally 16, 18 or 21.

How long can I rent a holiday home in Hillside for?

The length of time you can rent a holiday home in Hillside is up to the property. Just enter your chosen travel dates to view a list of options offering extended stays. With tons of creature comforts such as air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to get a terrific place to call your home away from home in Hillside.

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