Des Plaines holiday rentals

We found 814 holiday rentals — enter your dates for availability
Discover a selection of 38 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:18 Dec - 25 Dec

Private kitchen
Interior
Exterior
Living area
Exceptional
(11 reviews)

NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!

Chicago

8% off
AU$9,993
for 7 nights, 1 home
AU$1,428 per night
includes taxes & fees
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
Outdoor dining
Dining
Living area
Private kitchen
Exceptional
(11 reviews)

Quick Access to O'Hare and Chicago downtown

Melrose Park

8% off
AU$3,410
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
Quick Access to O'Hare and Chicago downtown
Interior
Private kitchen
Interior
Interior
Exceptional
(27 reviews)

Stunning 6 BR Home * Chicago * Centrally Located

Chicago

8% off
AU$10,488
for 7 nights, 1 home
AU$1,498 per night
includes taxes & fees
Stunning 6 BR Home * Chicago * Centrally Located
Living area
Cozy Home
Room
Interior
Exceptional
(12 reviews)

Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking

Chicago

7% off
AU$4,858
for 7 nights, 1 home
AU$694 per night
includes taxes & fees
Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking
Interior
Frank Lloyd Wright Home and Studio 3 Min
Dining
Interior
Exceptional
(36 reviews)

A quiet stay while you are away

Oak Park

8% off
AU$1,644
for 7 nights, 1 home
AU$235 per night
includes taxes & fees
A quiet stay while you are away
Living area
Interior
Interior
Private kitchen
Wonderful
(90 reviews)

Chic, Cozy home, by Blue Line Train Stop + Free parking

Chicago

5% off
AU$1,751
for 7 nights, 1 apartment
AU$250 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior
Breakfast bar seating also available
Master bedroom w/king size memory foam bed
Open concept kitchen
Exceptional
(23 reviews)

Wonderful in Wood Dale, right by O’Hare airport!

Wood Dale

13% off
AU$4,826
for 7 nights, 1 home
AU$689 per night
includes taxes & fees
Wonderful in Wood Dale, right by O’Hare airport!
Dining
Interior
Private kitchen
Room
Exceptional
(18 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
AU$2,618
for 7 nights, 1 apartment
AU$374 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Bedroom
Interior
Mini pool fun for young and old.
Spacious garage fits two cars.
Exceptional
(24 reviews)

Top floor of Historic Oak Park Home /2 Car Garage

Oak Park

12% off
AU$3,161
for 7 nights, 1 apartment
AU$452 per night
includes taxes & fees
Top floor of Historic Oak Park Home /2 Car Garage
Room
Room
Private kitchen
Private kitchen
Exceptional
(16 reviews)

Modern Deluxe Studio Suite in lovely Oak Park!

Oak Park

7% off
AU$1,690
for 7 nights, 1 apartment
AU$241 per night
includes taxes & fees
Modern Deluxe Studio Suite in lovely Oak Park!
Exterior
Interior
Living area
Room
Very good
(21 reviews)

Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.

Chicago

7% off
AU$2,150
for 7 nights, 1 apartment
AU$307 per night
includes taxes & fees
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.

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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 Navy Pier 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)
  • LEGOLAND® Discovery Center (7.7 mi / 12.5 km)
  • Chevy Chase Country Club (8.8 mi / 14.2 km)
  • The Water Works Indoor Water Park (12 mi / 19.3 km)
  • Hilldale Golf Club (12.2 mi / 19.6 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)
  • Heritage Park (7.3 mi / 11.8 km)
  • Portage Park (8.2 mi / 13.1 km)
  • Chicago Botanic Garden (9.3 mi / 14.9 km)
  • Humboldt Park (12.8 mi / 20.7 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 best area to stay in Des Plaines when booking a holiday rental?
When considering the best area to stay in Des Plaines, Illinois, for a holiday rental, the downtown area stands out as an excellent choice. This vibrant neighbourhood offers a charming mix of local shops, restaurants, and easy access to public transport, making it convenient for exploring the wider region. One of the top attractions nearby is the Rivers Casino, which provides entertainment options including gaming, dining, and live performances. Additionally, the beautiful Lake Opeka is a lovely spot for outdoor activities, such as picnicking, fishing, or simply enjoying a peaceful walk by the water.Another appealing neighbourhood to consider is the area around the Des Plaines River. This scenic locale not only offers a variety of properties for rent but also boasts access to picturesque trails for hiking and cycling, ideal for those who enjoy spending time outdoors. The proximity to the River Trails Park is particularly attractive for families and nature enthusiasts, providing ample opportunities for recreation and relaxation.*You must be at least 18 years old to participate in gambling activities in the United Kingdom. Please gamble responsibly. If you feel that gambling is affecting your life, seek help from organisations such as BeGambleAware at www.begambleaware.org or call their helpline at 0808 8020 133.
What is the most popular type of holiday rental accomodation in Des Plaines?
In Des Plaines, holiday houses are the predominant type of holiday rental, with approximately 108 available across the area. These homes typically feature multiple bedrooms, spacious living areas, and well-equipped kitchens, making them ideal for families or groups seeking a comfortable and home-like atmosphere. Many of these houses also include outdoor spaces for relaxation and gathering. In addition to holiday houses, there are around 15 apartments, which offer a more compact and convenient option for travellers, often including basic amenities such as kitchenettes and dining areas. While villas are less common, a few can be found in the area, providing additional choices for those looking for a more upscale stay.
Are there any family house rentals in Des Plaines?
In Des Plaines, Illinois, there are numerous family-friendly house rentals available—specifically around 20 options throughout the area. This suburban locale is ideal for families, with many properties offering spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces suitable for children to play. Common amenities include Wi-Fi and air conditioning, ensuring a comfortable stay for all.Families will appreciate the proximity to local attractions, including the Des Plaines River and various parks, which provide opportunities for outdoor activities such as picnicking and walking trails. Additionally, the nearby Chicago area offers cultural experiences and entertainment options, making Des Plaines a convenient base for exploring the greater region.
Can I rent a holiday home with a pool or hot tub in Des Plaines?
In Des Plaines, there are several holiday homes available for rent that feature pools and hot tubs. This suburban area, located just northwest of Chicago, offers a mix of residential charm and easy access to urban amenities. Many of these properties can be found in quiet neighbourhoods, providing a relaxing atmosphere for families or groups.Travellers can expect a variety of amenities in these rentals, including private pools, hot tubs for unwinding after a long day, and outdoor spaces great for gatherings. Fully equipped kitchens are common, allowing for convenient meal preparation, and many homes also offer spacious living areas and modern conveniences such as Wi-Fi and air conditioning.
Are there pet-friendly house rentals in Des Plaines?
In Des Plaines, there are several pet-friendly house rentals available, offering a great selection for travellers with furry companions. Many of these properties are equipped with modern amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces, making them ideal for families or groups.The area is conveniently located near several parks, including the picturesque Lake Opeka, which features walking paths and open green spaces superb for enjoying outdoor activities with pets. Additionally, the nearby Des Plaines River Trail offers scenic routes for walking or biking, allowing pet owners to explore the natural beauty of the region.
Are there any remote work holiday rentals in Des Plaines?
In Des Plaines, Illinois, there are numerous options for remote work holiday rentals, with around 114 available throughout the area. These properties cater well to professionals seeking a comfortable workspace away from home. Many rentals feature high-speed Wi-Fi, ensuring seamless connectivity for video calls and online tasks. Some accommodations also provide dedicated workspaces, allowing for a productive environment.Travellers can expect a variety of amenities such as fully equipped kitchens for self-catering, spacious living areas, and comfortable bedrooms to unwind after a long day. The area is conveniently located near local parks, restaurants, and shops, providing opportunities for relaxation and leisure outside of work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Des Plaines?
In Des Plaines, popular rental amenities include kitchens, which allow guests to prepare their own meals, and onsite parking for added convenience. Many properties also feature coffee and tea makers, superb for those who enjoy a warm beverage at any time. Furthermore, a top number of rentals are pet-friendly, accommodating travellers who wish to bring their furry companions along, including service animals.
When is the best time to visit Des Plaines for a holiday rental?
The peak season for visiting Des Plaines is during the summer months, particularly from June to August, when the weather is warm and inviting. This is a fantastic time for families and outdoor enthusiasts, as you can enjoy local parks, vibrant festivals, and various recreational activities. The sunny days, with temperatures often reaching the mid-20s to low 30s Celsius, create a great backdrop for exploring the area's attractions.July stands out as the most popular month, bustling with visitors eager to take advantage of the summer vibes. You can immerse yourself in the local culture, partake in outdoor events, or simply relax in the beautiful surroundings of Des Plaines.For those looking for a more budget-friendly experience, consider visiting in December. While this month may be quieter, it offers a unique charm, especially for those who appreciate festive decorations and holiday events. The serene atmosphere provides an excellent opportunity for cosy indoor activities and exploring the local dining scene.Ultimately, the best time to book a holiday rental in Des Plaines will depend on your preferences.
What are the top attractions in Des Plaines?
In Des Plaines, visitors can explore several top attractions that reflect the area's charm. One of the highlights is the Riverwalk, a scenic pathway along the Des Plaines River, great for leisurely strolls and enjoying the outdoors. Nearby, the Woodfield Mall in Schaumburg, just a short drive away, is one of the largest shopping centres in the United States, offering a wide range of shops and dining options.The Des Plaines History Centre provides insights into the local heritage, featuring exhibits and historical artifacts that tell the story of the community. Additionally, the city is home to the popular Mystic Waters Family Aquatic Centre, ideal for families during the summer months. For nature enthusiasts, the nearby Busse Woods, located in Elk Grove Village, offers extensive trails for hiking, biking, and wildlife observation.Moreover, the Park District hosts various events and activities throughout the year, contributing to the vibrant community atmosphere.
Are all fees included in the Des Plaines holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Des Plaines holiday homes with parking?
Stayz offers a wide selection of holiday homes in Des Plaines with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Des Plaines holiday homes?
You can find great discounts on holiday homes in Des Plaines on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Des Plaines holiday home booking on Stayz?
To find Des Plaines holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Des Plaines?
A long-stay holiday home in Des Plaines is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Des Plaines holiday home?
Book your Des Plaines holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Des Plaines?
Prices for holiday homes in Des Plaines vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Des Plaines to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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