North Side holiday lettings

We found 2,333 holiday rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
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Book a holiday rental for your North Side getaway

Learn about the unique charm of North Side with a stay in a holiday home rental. This city has something for everyone. Wrigley Field and Lake Michigan are just a couple of the must-see attractions. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around North Side

Do you want to discover things to do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes North Side a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Lincoln Park Zoo (2.4 mi / 3.9 km)
  • Home Alone House (12.5 mi / 20.1 km)
  • The Glen Club (13.3 mi / 21.4 km)
  • Oak Brook Golf Course (14.5 mi / 23.3 km)
  • Northbrook Sports Complex (15.7 mi / 25.2 km)
  • TopGolf Chicago (16.8 mi / 27.1 km)

Exploring the natural features in North Side

Whether you're an active traveller or just want to appreciate the scenery, North Side is a great spot to appreciate mother nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Grant Park (5.1 mi / 8.2 km)
  • Millennium Park (4.5 mi / 7.2 km)
  • The 606 (1.7 mi / 2.7 km)
  • Lincoln Park (2.3 mi / 3.6 km)
  • Humboldt Park (2.3 mi / 3.7 km)
  • North Avenue Beach (3 mi / 4.7 km)

Travelling to and around North Side

If you'd prefer to travel by train, you can make your way to Chicago Clybourn Station. You can get around North Side by jumping on the metro at Paulina Station, Addison Station (Brown Line) or Southport Station.

Frequently asked questions

What is the most popular type of holiday rental accommodation in North Side?

According to our data, apartments are the most popular holiday rental type in North Side. But as you might expect, everyone's idea of the perfect stay isn't going to be the same. Vrbo has holiday rentals of all sizes, shapes and budgets, and we'll help you locate your ideal fit.

How much does it cost to rent a holiday rental in North Side?

Several things can influence what you'll pay for a holiday rental in North Side, such as the type of property, season and length of stay. Still, all Vrbo homes have one thing in common — excellent value. Just add your travel dates to find your dream escape.

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

Prices for beach houses in North Side differ depending on the type and size of the property and when you plan to travel. All you have to do is enter your travel dates into Vrbo and how many guests to see available options and prices. From there you can use our filter tool to narrow your search by ratings, amenities, nearby activities and more.

Are there pet-friendly holiday rentals in North Side?

Pack a suitcase for the pooch in your life because North Side has 312 stays that welcome pets with open arms. Let your four-legged friend have fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your dates then check our "Pets allowed" filter box.

Can I rent a house with a pool in North Side?

Add a whole new level of fun to your getaway by booking your crew into one of the 20 houses with a private pool in North Side. Use our search filter to find the kind of property you want on Vrbo, and then spend carefree days splashing about in a swimming pool that's for your use only.

What are popular rental amenities in North Side?

When it comes to rental amenities that guests are on the lookout for in North Side, a swimming pool, a barbecue grill and an electric car charging station are the most popular. With Vrbo holiday rentals, there are options to fit your taste and style, whether you're on a trip with family members, friends or even pets.

Are there large group holiday rentals in North Side?

North Side has 36 holiday rentals that can cater to 10 or more guests. These properties come with the space you need to share good times with family and friends.

Are there holiday rentals in North Side that welcome kids?

Bring the entire group together for an adventure in North Side at one of our 310 family-friendly properties. These stays provide conveniences that are perfect for getaways with children, including laundry facilities, multiple bedrooms and swimming pools. Simply click on the "Properties good for families" filter and decide on your favourite.

What are the top attractions for families in North Side?

You'll find loads of awesome things to do and see with the family in North Side, including:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday rentals in North Side?

Take your pick from 78 one-bedroom rentals in North Side. Whether you'd like a comfy cottage or an upmarket condo, Vrbo's one-bedroom properties are just right if you don't require a huge amount of space. One of the best parts about having your own pad? You won't ever need to share your trip with strangers.

Can I find two-bedroom holiday rentals in North Side?

North Side has 109 two-bedroom properties to pick from. Go for a holiday home with all the comfort and space you need at a price that won't break the bank on Vrbo.

Are there holiday rentals with WiFi in North Side?

Whether you want to keep up with the news, write a few emails or post a pic to social media, there are 83 holiday homes with WiFi in North Side. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

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