Des Plaines holiday rentals

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July 2025

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Discover a selection of 31 homes and other holiday rentals in Des Plaines that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you need and want for your stay, which might include parking and a washer and dryer. At the end of the day, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Des Plaines

Showing deals for:17 Oct - 24 Oct

Exceptional

(31 reviews)

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Skokie, IL

9% off

S$701 per night

includes taxes & fees

Indulge in lavish outdoor living with ample seating, firepit, and daybed.

Exceptional

(5 reviews)

Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown

Chicago, IL

11% off

S$520 per night

includes taxes & fees

We are proud that our home boasts one of the largest yards in all of Chicago!

Exceptional

(14 reviews)

Luxe Duplex - Private Gym -Huge Yard -King Beds Garage Parking-EV Charger- Crib

Chicago, IL

19% off

S$529 per night

includes taxes & fees

Exceptional

(7 reviews)

Pulaski Mahal - Spacious 3bed/2.5bath with Game Room. Close to Hwy, train.

Chicago, IL

7% off

S$574 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Des Plaines

Showing deals for: 17 Oct - 20 Oct

Family fun-house w/POOL & Game Room, 5 min from Airport and Rosement attractions

Sleeps 8 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 home

S$622 per night

includes taxes & fees

Des Plaines Vacation Rental | 3BR | 1BA | Stairs Required to Enter | 740 Sq Ft

Des Plaines Vacation Rental w/ Spacious Backyard!

Sleeps 6 · 3 bedrooms · 1 bathroom

for 3 nights, 1 home

S$367 per night

includes taxes & fees

Huge 4BR w/ Yard | Sleeps 8 | LCP Collection

Sleeps 8 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 home

S$826 per night

includes taxes & fees

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 captivating area of Des Plaines awaits your stay

Come and experience Des Plaines and its entertainment, opera and theatre scene. Renowned for its restaurants, sporting events and shopping, this city welcomes all visitors. Wrigley Field and Michigan Avenue are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Des Plaines

Are you looking for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Des Plaines a fun spot to go on holiday. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

The Glen Club (4.9 mi / 7.8 km)
Northbrook Sports Complex (6.3 mi / 10.2 km)
Pirates Cove Childrens Theme Park (7 mi / 11.3 km)
LEGOLAND® Discovery Center (7.7 mi / 12.5 km)
Chevy Chase Country Club (8.8 mi / 14.2 km)
Lincoln Park Zoo (15 mi / 24.1 km)

Exploring the natural features in Des Plaines

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Des Plaines. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

Millennium Park (17 mi / 27.3 km)
Grant Park (17.5 mi / 28.1 km)
Portage Park (8.2 mi / 13.1 km)
Chicago Botanic Garden (9.3 mi / 14.9 km)
North Shore Beach Park (11.8 mi / 19 km)
Kathy Osterman Beach (12.3 mi / 19.8 km)

Transport to and around Des Plaines

The nearest airport is in Chicago O'Hare International Airport (ORD), located 4 mi (6.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Chicago, IL (PWK-Chicago Executive), which is 5.8 mi (9.4 km) away.

If you're travelling by train, make your way to Des Plaines Station or Des Plaines Cumberland Station and explore the city from there.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Des Plaines?

Houses are the most popular type of holiday rental in Des Plaines, according to our data. Even if you have something else in mind, Vrbo has properties in all sizes and shapes. Browse our many options to find your perfect fit.

How much does it cost to rent a holiday rental in Des Plaines?

The average price for a holiday home in Des Plaines depends on a number of factors, including length of stay, property type and season. Whether you're dreaming about a sprawling villa with lots of bedrooms or a quaint cottage that's perfect for two, just add your travel dates to see stays with terrific value.

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

Prices for beach houses in Des Plaines may differ depending on the size and type of the property and time of year you're travelling. All you need to do is enter your travel dates into Vrbo and how many guests to see your rental options and prices. From there you can use our filters to narrow your search results by nearby activities, amenities, ratings and more.

Are there pet-friendly holiday rentals in Des Plaines?

There are, yes. You'll have a choice of eight holiday homes that welcome pets in Des Plaines on Vrbo. Our furry best friends deserve a break too, so simply use our search function for pet-friendly holiday rentals to find a perfect property where your doggie can join the fun.

What are popular rental amenities in Des Plaines?

A fireplace, nearby museums and a garden are rated the most popular rental amenities in Des Plaines. Whether you plan to go as a party of one, with your significant other or a bunch of friends, Vrbo can help you find a holiday home that fits your style with a load of extras you'll love.

Are there large group holiday rentals in Des Plaines?

With three Des Plaines holiday homes that can host a group of five or more people, you can bring a few extra family members or pals along. Whether you're planning a casual get-together or a celebratory event, Vrbo will help you book the ideal space for the occasion.

Are there holiday rentals in Des Plaines that welcome kids?

Des Plaines has eight family-friendly holiday rentals. And finding a stay that welcomes little ones is easy with our "Properties good for families" filter. Besides having the whole place to yourselves, you'll get conveniences and perks like multiple bedrooms, private pools and yards.

What are the top attractions for families in Des Plaines?

There are tons of wonderful things to see and do with the family in Des Plaines, such as:

Parkway Bank Park Entertainment District
Kohl Childrens Museum
Orbit Skate Centre

Can I find two-bedroom holiday rentals in Des Plaines?

Take off with your besties and enjoy a relaxing escape in one of the two two-bedroom holiday homes Des Plaines has to offer.

Are there holiday rentals with WiFi in Des Plaines?

You'll have a choice of seven holiday rentals with WiFi in Des Plaines. If you'd like to disconnect from daily life on your holiday, but still want to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find holiday rentals with air conditioning in Des Plaines?

You'll have your pick of six holiday homes with air conditioning in Des Plaines giving you that cool, cool breeze and extra bit of comfort. Enter your dates of travel and then take advantage of our filter tool to locate properties with air conditioning.

How old do you have to be to rent a holiday rental in Des Plaines?

The minimum age can differ across properties on Vrbo, so be sure to look at the rules of the holiday home in Des Plaines you're considering. But normally, it's 16, 18 or 21.

How long can I rent a holiday rental in Des Plaines for?

It's up to the Des Plaines property. To view all available options offering extended stays, simply type your travel dates and number of guests into Vrbo. You can enjoy having the place to yourself, along with comforts such as a fully-equipped kitchen and outdoor spaces where the kids can run and play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.