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Hillside vacation rentals

We found 551 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Scroll through and select from vacation rentals in Hillside to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

Houses

Houses
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    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, yards and more
  • More for less
    More space, more privacy, more amenities — more value

The tranquil area of Hillside awaits your stay

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

Activities and attractions in Hillside

Are you hoping to find attractions to see while you're in town? Venture out of your cozy vacation rental and experience everything that makes Hillside a fun place to get away. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • The Dome at the Parkway Bank Sports Complex (7.3 mi / 11.7 km)
  • TopGolf Chicago (8.8 mi / 14.2 km)
  • Seven Bridges Golf Club (11.5 mi / 18.4 km)
  • LEGOLAND® Discovery Center (13.1 mi / 21 km)
  • Cantigny Golf Club (13.2 mi / 21.2 km)
  • Dave & Buster's (14.1 mi / 22.6 km)

Exploring the natural landscape of Hillside

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Hillside. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • 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)

Traveling to and around Hillside

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

Frequently asked questions

What is the most popular type of vacation rental accommodation in Hillside?

The most desirable types of vacation rentals 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 vacation rental in Hillside?

The average price for a vacation 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 vacation rental in Hillside?

You'll need to check with the Hillside vacation rental 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 vacation rental in Hillside for?

The length of time you can rent a vacation rental 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.