Near West Side holiday rentals

We found 975 holiday rentals — enter your dates for availability

Discover a selection of 283 apartments, 18 flats and other holiday rentals in Near West Side that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Near West Side

Showing deals for:12 Dec - 19 Dec

Image gallery for Beautiful Downtown 3BR with Free Parking

Living area
9.6 out of 10 rating
Exceptional
(21 reviews)

Beautiful Downtown 3BR with Free Parking

Chicago, IL

7% off
Price is AU$6,018
for 7 nights, 1 apartment
AU$860 per night
includes taxes & fees
Beautiful Downtown 3BR with Free Parking

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

Frequently asked questions

What is the most popular type of holiday home accommodation in Near West Side?
Based on our data, apartments are considered the most popular type of holiday property in Near West Side. But naturally, everyone's idea of an awesome stay isn't going to be the same. Stayz has holiday homes of all shapes, sizes and budgets, so you're sure to discover the perfect fit.
How much does it cost to rent a holiday home in Near West Side?
Length of stay, property type and season are some factors that can affect the price of a holiday home. Simply add your dates of travel to find your ideal match. From cosy chalets to plush villas, all Stayz holiday homes offer amazing value.
How much does it cost to rent a beach house in Near West Side?
The average price for a holiday home near the beach in Near West Side will depend on when you're going and the size and type of property you're looking for. You can find prices quickly and easily on Stayz by entering your dates of travel. Then use our handy filter tool to choose the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday homes in Near West Side?
Yes, there are. You can choose from 159 holiday homes that allow pets in Near West Side on Stayz. Our cuddly best friends also need a break, so simply use our search function for pet-friendly holiday homes to find a property where your puppy dog can share in the good times.
Can I rent a house with a pool in Near West Side?
Dig out your swimsuit and inflatable flamingo, because there are 48 houses with a private pool in Near West Side. Stay at one of these popular holiday homes and you'll enjoy pool days every day. Simply enter your travel dates into Stayz, then use the "pool" filter to find a place to make a splash!
What are popular home amenities in Near West Side?
Some of the most popular home amenities guests are looking for in Near West Side include a nearby river, a garden and a fireplace. Whether you're going on holiday with pals, family or even pets, Stayz holiday properties include the best amenities for starting a new adventure with the people that matter most.
Are there large group holiday homes in Near West Side?
With 11 properties that can host 10 or more people in Near West Side, you won't have to leave anyone off your guest list. From holidays with the extended family to events like birthday parties and weddings, Stayz can help you find a large group home that fits the occasion.
Are there holiday homes in Near West Side that welcome kids?
Bring the whole group together for a memorable adventure in Near West Side at one of our 159 family-friendly holiday properties. Many of these stays provide amenities that are ideally suited to trips with children, including laundries, living rooms and swimming pools. Simply click on the "Properties good for families" filter and pick out your favourite.
What are the top attractions for families in Near West Side?
Keeping the kids occupied during your stay in Near West Side is simple with these cool family-friendly attractions:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday homes in Near West Side?
Yes, you can take your pick from 72 one-bedroom homes in Near West Side. Whether you'd prefer a cosy cottage or a condo, our one-bedroom homes are ideal if you don't require lots of room. One of the best things about having your own digs? You won't need to share your adventure with strangers.
Can I find two-bedroom holiday homes in Near West Side?
You can pick from 29 two-bedroom homes in Near West Side. Settle the kids into the second room or maybe fill it with a couple of your nearest and dearest friends. There's enough space for whoever's fortunate enough to come along for the ride.
Are there holiday homes with WiFi in Near West Side?
Choose from 19 holiday homes with WiFi in Near West Side. If you'd like to disconnect from the world on your holiday, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Near West Side?
You'll have a choice of 157 holiday homes with air conditioning in Near West Side offering that cool, cool breeze and extra bit of comfort. Simply enter your preferred travel dates and then use our handy filters to find stays with air conditioning.
How old do you have to be to rent a holiday home in Near West Side?
The minimum age can differ across properties on Stayz, so look at the rules of the holiday home in Near West Side you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Near West Side for?
It's up to the Near West Side property. To look at a list of options offering extended stays, just type your dates and guest number into Stayz. Enjoy having the entire place to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and a backyard to play in. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.

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