Rosemont holiday rentals

We found 827 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Rosemont that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Rosemont

Showing deals for:18 Dec - 25 Dec

Living area
Interior
Exterior
Private kitchen
Exceptional
(11 reviews)

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

Chicago

8% off
AU$10,218
for 7 nights, 1 home
AU$1,460 per night
includes taxes & fees
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
Private kitchen
Dining
Living area
Room
Exceptional
(11 reviews)

Quick Access to O'Hare and Chicago downtown

Melrose Park

8% off
AU$3,430
for 7 nights, 1 home
AU$490 per night
includes taxes & fees
Quick Access to O'Hare and Chicago downtown
Dining
Interior
Living area
Private kitchen
Exceptional
(40 reviews)

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
AU$2,898
for 7 nights, 1 apartment
AU$414 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Interior
Private kitchen
Interior
Exterior
Exceptional
(27 reviews)

Stunning 6 BR Home * Chicago * Centrally Located

Chicago

8% off
AU$10,879
for 7 nights, 1 home
AU$1,554 per night
includes taxes & fees
Stunning 6 BR Home * Chicago * Centrally Located
Room
Cozy Home
Living area
Interior
Exceptional
(12 reviews)

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

Chicago

7% off
AU$4,887
for 7 nights, 1 home
AU$698 per night
includes taxes & fees
Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking
Interior
Dining
Private kitchen
Interior
Exceptional
(8 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off
AU$5,196
for 7 nights, 1 home
AU$742 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Dining
Living area
Private kitchen
Room
Exceptional
(22 reviews)

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Berwyn

8% off
AU$2,613
for 7 nights, 1 apartment
AU$373 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Living area
Interior
Living area
Room
Exceptional
(24 reviews)

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Berwyn

8% off
AU$2,543
for 7 nights, 1 apartment
AU$363 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Living area
Interior
Room
Private kitchen
Wonderful
(91 reviews)

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

Chicago

5% off
AU$1,744
for 7 nights, 1 apartment
AU$249 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior
Breakfast bar seating also available
Open concept kitchen
Fully fenced yard - perfect for fur babies
Exceptional
(23 reviews)

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

Wood Dale

13% off
AU$4,855
for 7 nights, 1 home
AU$694 per night
includes taxes & fees
Wonderful in Wood Dale, right by O’Hare airport!
Interior
Frank Lloyd Wright Home and Studio 3 Min
Dining
Room
Exceptional
(36 reviews)

A quiet stay while you are away

Oak Park

8% off
AU$1,653
for 7 nights, 1 home
AU$236 per night
includes taxes & fees
A quiet stay while you are away
Interior
Interior
Room
Dining
Exceptional
(18 reviews)

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

Chicago

7% off
AU$2,614
for 7 nights, 1 apartment
AU$373 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Bedroom
Interior
Spacious garage fits two cars.
Mini pool fun for young and old.
Exceptional
(24 reviews)

Top floor of Historic Oak Park Home /2 Car Garage

Oak Park

12% off
AU$3,180
for 7 nights, 1 apartment
AU$454 per night
includes taxes & fees
Top floor of Historic Oak Park Home /2 Car Garage
Private kitchen
Room
Exterior detail
Room
Exceptional
(16 reviews)

Modern Deluxe Studio Suite in lovely Oak Park!

Oak Park

7% off
AU$1,700
for 7 nights, 1 apartment
AU$243 per night
includes taxes & fees
Modern Deluxe Studio Suite in lovely Oak Park!
Living area
Interior
Room
Exterior
Very good
(21 reviews)

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

Chicago

7% off
AU$2,163
for 7 nights, 1 apartment
AU$309 per night
includes taxes & fees
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
Living area
Room
Bathroom
Dining
Exceptional
(13 reviews)

Chic & Cozy near ORD>MDW>DT>HOSP

Berwyn

8% off
AU$3,299
for 7 nights, 1 apartment
AU$471 per night
includes taxes & fees
Chic & Cozy near ORD>MDW>DT>HOSP

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The captivating city of Rosemont awaits you

The area's entertainment and theatre scene are just some of the reasons to come on holiday to Rosemont. Renowned for its hockey games, shopping and restaurants, this city welcomes all visitors. Wrigley Field and Navy Pier are just a couple of the must-see attractions in the area. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Rosemont

Are you hoping to discover top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Rosemont has to offer. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • The Glen Club (7.4 mi / 11.9 km)
  • LEGOLAND® Discovery Center (9 mi / 14.6 km)
  • Northbrook Sports Complex (9.3 mi / 14.9 km)
  • Galloping Ghost (11.9 mi / 19.1 km)
  • Chevy Chase Country Club (12 mi / 19.3 km)
  • The Water Works Indoor Water Park (13 mi / 20.9 km)

Exploring the natural features in Rosemont

Whether you're looking for adventure or just want to take in the scenery, Rosemont is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (14.7 mi / 23.7 km)
  • Grant Park (15.2 mi / 24.4 km)
  • Portage Park (6 mi / 9.6 km)
  • Humboldt Park (10.4 mi / 16.8 km)
  • Heritage Park (10.5 mi / 16.9 km)
  • Garfield Park Conservatory (10.6 mi / 17.1 km)

Transport to and around Rosemont

Fly into Chicago O'Hare International Airport (ORD), the closest airport, located 1.9 mi (3 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Chicago, IL (PWK-Chicago Executive), which is 9 mi (14.4 km) away.

If you prefer train travel, make your way to Rosemont O'Hare Transfer Station or Rosemont Station and explore the city from there. You can see more of Rosemont by catching a ride on the metro at O'Hare Multi-Modal Facility Station, Multi-Modal Facility Station or Rosemont Station.

Frequently asked questions

What is the best area to stay in Rosemont when booking a holiday rental?
When considering a holiday rental in Rosemont, Illinois, a popular area to stay is near the vibrant entertainment district. This neighbourhood is known for its diverse array of dining options, shopping venues, and proximity to key attractions. Notably, the Rosemont Theatre often hosts a variety of performances, making it a cultural hub in the area. Additionally, the nearby Fashion Outlets of Chicago provide an excellent shopping experience with a range of brand-name stores, superb for those who enjoy retail therapy.Another appealing aspect of this district is its accessibility to public transport, which makes it easy to explore the wider Chicago area. The availability of holiday rentals in this part of Rosemont is quite substantial, offering a mix of options that cater to different budgets and preferences.
What is the most popular type of holiday rental accomodation in Rosemont?
In Rosemont, apartments and condos are the most popular types of holiday rentals, with several options available throughout the area. These accommodations are typically situated near attractions such as the Rosemont Theatre and the Fashion Outlets of Chicago, providing convenient access to shopping and entertainment. Most units feature modern amenities, including fully equipped kitchens, comfortable living spaces, and often access to shared facilities like fitness centres or pools.
Are there any family house rentals in Rosemont?
In Rosemont, Illinois, there are several family-friendly house rentals available, making it a great choice for those travelling with children. Properties in this area often provide spacious living arrangements, fully equipped kitchens for preparing meals, and comfortable outdoor spaces where families can relax. Many homes come with conveniences like Wi-Fi and laundry facilities, ensuring a straightforward stay.The locale is conveniently located near attractions such as the Rosemont Theatre, a hub for family-friendly performances, and the nearby Park at Rosemont, which features playgrounds and walking trails superb for outdoor activities. Additionally, the Fashion Outlets of Chicago are just a short drive away, offering shopping opportunities for all ages.
Are there pet-friendly house rentals in Rosemont?
In Rosemont, there are several pet-friendly house rentals available, making it an excellent choice for travellers accompanied by their furry companions. Many of these holiday homes come equipped with modern amenities such as spacious living areas, fully stocked kitchens, and outdoor patios, providing comfort and convenience for families or groups.The area features easy access to several parks, including the nearby Des Plaines River Trail, which is ideal for walking and enjoying the outdoors with pets. Additionally, the Rosemont Theatre and the Parkway Bank Park Theatre offer entertaining options for visitors, adding to the vibrant setting of the area.
Are there any remote work holiday rentals in Rosemont?
In Rosemont, Illinois, there are several holiday rentals available that cater to remote work needs. Many of these properties are equipped with amenities such as high-speed Wi-Fi, dedicated workspace areas, and comfortable desks, ensuring a productive environment for those working away from home.The area is conveniently located near O'Hare International Airport, making it an ideal choice for business travellers. Additionally, Rosemont is home to various dining and entertainment options, including the Fashion Outlets of Chicago and the Donald E. Stephens Convention Centre, providing a great balance of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Rosemont?
In Rosemont, popular holiday rental amenities reflect a focus on comfort and convenience. Travellers can expect properties equipped with kitchens, allowing for self-catering, and air conditioning to ensure a pleasant stay, especially during warmer months. Many rentals also feature desks, making them suitable for work or study. Families will appreciate the presence of children's books, providing entertainment for younger guests. Additionally, some accommodations may include blenders, superb for preparing smoothies or other refreshments.
When is the best time to visit Rosemont for a holiday rental?
September is the most popular time to visit Rosemont, Illinois, making it an ideal choice for those seeking a holiday rental. This month falls within the peak season, which spans from July to September, when the weather is pleasantly warm and outdoor activities abound. With temperatures typically ranging from 15 to 25 degrees Celsius, visitors can comfortably enjoy the area's attractions, including the bustling Rosemont Entertainment District and the nearby Fashion Outlets of Chicago.During September, you'll find a vibrant setting as events and festivals take place, drawing both tourists and locals alike. It's a great time to explore the local dining scene, catch a show at the Rosemont Theatre, or simply stroll along the scenic Des Plaines River.If you're looking for a more budget-friendly option, consider planning your visit in December. During this time, this month offers a unique charm with holiday decorations and seasonal events that can provide a delightful experience.
What are the top attractions in Rosemont?
In Rosemont, visitors can explore a variety of attractions that cater to different interests. The Rosemont Theatre is a major venue for concerts and performances, drawing crowds for various shows throughout the year. Nearby, the Parkway Bank Park Entertainment District offers a mix of dining, nightlife, and live music, making it a lively spot for evening outings.For those interested in shopping, the Fashion Outlets of Chicago provide a range of designer brands at discounted prices, appealing to fashion enthusiasts and bargain hunters alike. The area is also home to the Donald E. Stephens Convention Centre, which hosts a number of events and exhibitions, contributing to the vibrant setting of Rosemont.Nature lovers can enjoy a stroll at the nearby Riverwalk or visit the nearby parks for some outdoor activities.
Are all fees included in the Rosemont 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 Rosemont holiday homes with parking?
Stayz offers a wide selection of holiday homes in Rosemont 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 Rosemont holiday homes?
You can find great discounts on holiday homes in Rosemont 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 Rosemont holiday home booking on Stayz?
To find Rosemont 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 Rosemont?
A long-stay holiday home in Rosemont 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 Rosemont holiday home?
Book your Rosemont 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 Rosemont?
Prices for holiday homes in Rosemont 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 Rosemont 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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