Berwyn holiday rentals

We found 2,965 holiday rentals — enter your dates for availability
Discover a selection of 14 homes, 25 apartments and other holiday rentals in Berwyn that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include a hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Berwyn

Showing deals for:29 Jan - 5 Feb

Interior
Exceptional
(42 reviews)

Chicago Gold Coast Mansion 6 Bed Luxury Retreat

Chicago

7% off
AU$24,723
for 7 nights, 1 home
AU$3,532 per night
includes taxes & fees
Chicago Gold Coast Mansion 6 Bed Luxury Retreat
Our downtown Townhouse is in an amazing location
Exceptional
(93 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
AU$6,520
for 7 nights, 1 home
AU$931 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Private kitchen
Exceptional
(17 reviews)

5 bedrooms/ 3 bathrooms/2 living rooms Elegant Escape at Burr Ridge/ La Grange

Burr Ridge

8% off
AU$5,021
for 7 nights, 1 home
AU$717 per night
includes taxes & fees
5 bedrooms/ 3 bathrooms/2 living rooms Elegant Escape at Burr Ridge/ La Grange
River North Luxury Living
Exceptional
(107 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
AU$4,724
for 7 nights, 1 apartment
AU$675 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Exterior
Exceptional
(27 reviews)

Beautiful Berwyn Bungalow Close to Downtown Chicago

Berwyn

8% off
AU$3,423
for 7 nights, 1 home
AU$489 per night
includes taxes & fees
Beautiful Berwyn Bungalow Close to Downtown Chicago
Interior
Exceptional
(26 reviews)

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

Berwyn

8% off
AU$1,467
for 7 nights, 1 apartment
AU$210 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Downstairs living area
Exceptional
(103 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$14,287
for 7 nights, 1 apartment
AU$2,041 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Dining
Exceptional
(9 reviews)

Modern 4-bedroom house in peaceful Westmont area

Westmont

8% off
AU$4,526
for 7 nights, 1 home
AU$647 per night
includes taxes & fees
Modern 4-bedroom house in peaceful Westmont area
Living area
Wonderful
(15 reviews)

Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12

Chicago

7% off
AU$4,056
for 7 nights, 1 apartment
AU$579 per night
includes taxes & fees
Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12
Living Room
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$4,780
for 7 nights, 1 home
AU$683 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Exceptional
(93 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$7,703
for 7 nights, 1 home
AU$1,100 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Private kitchen
Exceptional
(69 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
AU$4,667
for 7 nights, 1 apartment
AU$667 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Interior
Wonderful
(44 reviews)

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

Berwyn

8% off
AU$1,835
for 7 nights, 1 apartment
AU$262 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Living area
Wonderful
(9 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
AU$5,896
for 7 nights, 1 apartment
AU$842 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Private kitchen
Exceptional
(32 reviews)

Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed

Chicago

7% off
AU$2,176
for 7 nights, 1 home
AU$311 per night
includes taxes & fees
Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed
Living area
Wonderful
(15 reviews)

High-end 2Bdrm Garden Apt. Where Comfort Meets Style

Chicago

7% off
AU$2,092
for 7 nights, 1 apartment
AU$299 per night
includes taxes & fees
High-end 2Bdrm Garden Apt. Where Comfort Meets Style
Exterior detail
Exceptional
(12 reviews)

Historic feel, Modern comfort Walk to parks and food in beautiful Chicago

Chicago

6% off
AU$1,993
for 7 nights, 1 apartment
AU$285 per night
includes taxes & fees
Historic feel, Modern comfort Walk to parks and food in beautiful Chicago
Dining
Exceptional
(10 reviews)

The Dakin Estate: 4BR Art Deco speakeasy duplex in Wrigleyville, 5 min from Wrigley Field. Designed for groups, it blends curated interiors, elevated finishes, and entertainment-focused spaces for Cubs games, concerts, and Chicago nightlife.

Chicago

6% off
AU$6,949
for 7 nights, 1 apartment
AU$993 per night
includes taxes & fees
The Dakin Estate: 4BR Art Deco speakeasy duplex in Wrigleyville, 5 min from Wrigley Field. Designed for groups, it blends curated interiors, elevated finishes, and entertainment-focused spaces for Cubs games, concerts, and Chicago nightlife.
Living area
Very good
(5 reviews)

Chicago style apt/Near Hosp/ORD/MDW/DT

Berwyn

8% off
AU$1,539
for 7 nights, 1 apartment
AU$220 per night
includes taxes & fees
Chicago style apt/Near Hosp/ORD/MDW/DT
Living area
Wonderful
(23 reviews)

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Berwyn

8% off
AU$1,500
for 7 nights, 1 apartment
AU$214 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Upscale kitchen with an equally spacious dining room
Exceptional
(11 reviews)

23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown

Chicago

7% off
AU$3,376
for 7 nights, 1 apartment
AU$482 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Top floor kitchen and dining area
Exceptional
(36 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
AU$5,888
for 7 nights, 1 apartment
AU$841 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
Living area
Exceptional
(24 reviews)

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

Berwyn

8% off
AU$1,498
for 7 nights, 1 apartment
AU$214 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Property grounds
Exceptional
(117 reviews)

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Chicago

14% off
AU$2,391
for 7 nights, 1 apartment
AU$342 per night
includes taxes & fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

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The lively area of Berwyn awaits your stay

Come and experience Berwyn and its live music, churches and art galleries. Renowned for its shopping, restaurants and chocolate shops, this city welcomes all visitors. McCormick Place and Soldier Field are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Berwyn

Do you want to discover things to do during your stay? Venture out of your cosy holiday rental and experience everything that makes Berwyn a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Galloping Ghost (3.9 mi / 6.4 km)
  • Oak Brook Golf Course (7 mi / 11.3 km)
  • Lincoln Park Zoo (9.6 mi / 15.4 km)
  • The Dome at the Parkway Bank Sports Complex (9.9 mi / 16 km)
  • Cog Hill Golf & Country Club (14.8 mi / 23.8 km)
  • Harborside International Golf Center (14.9 mi / 23.9 km)

Exploring the natural features in Berwyn

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 Berwyn. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (9.1 mi / 14.6 km)
  • Grant Park (9 mi / 14.6 km)
  • Garfield Park (4.5 mi / 7.2 km)
  • Garfield Park Conservatory (4.6 mi / 7.5 km)
  • Anna and Frederick Douglass Park (4.9 mi / 7.9 km)
  • Humboldt Park (6 mi / 9.7 km)

Travelling to and around Berwyn

The nearest airport is in Chicago Midway Airport (MDW), located 5.1 mi (8.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Chicago O'Hare International Airport (ORD), which is 10.4 mi (16.8 km) away.

If you prefer to travel by train, Berwyn LaVergne Station, Berwyn Station and Berwyn Harlem Avenue Station are the main stations that serve the city.

Frequently asked questions

What is the best area to stay in Berwyn when booking a holiday rental?
When considering a holiday rental in Berwyn, Illinois, the area around the historic Depot District is an excellent choice. This vibrant neighbourhood is known for its charming architecture and an inviting space. The Depot District is not only the heart of Berwyn but also boasts a selection of delightful restaurants and cafes, great for enjoying local cuisine.A standout attraction in this area is the Berwyn Route 66 Museum, which offers a fascinating glimpse into the history of the iconic highway that runs through the heart of America. Additionally, the nearby Proksa Park provides a lovely green space for relaxation and outdoor activities, making it an ideal spot for families or those looking to unwind in nature.In terms of holiday rentals, the Depot District features a variety of properties that cater to different preferences and budgets, ensuring that visitors can find something that suits their needs.
What is the most popular type of holiday rental accomodation in Berwyn?
In Berwyn, holiday houses are the most popular type of holiday rental, with around 80 available throughout the area. These properties often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable home away from home. Additionally, about 60 apartments can be found, typically located in more urban settings, offering modern amenities and convenient access to local shops and dining options. For those looking for a smaller space, there are also around 12 condos, which often include communal amenities such as pools or fitness centres.
Are there any family house rentals in Berwyn?
In Berwyn, Illinois, there are numerous family-friendly house rentals available, with around 31 options to choose from. This vibrant community offers a range of properties that cater to families looking for a comfortable stay. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play.Visitors can enjoy the convenience of amenities such as Wi-Fi and air conditioning, ensuring that the stay is both enjoyable and relaxing. The neighbourhood is also close to local parks, which provide opportunities for outdoor activities and picnics. Additionally, Berwyn's proximity to Chicago allows for easy day trips to explore the city's attractions, such as museums and cultural landmarks.
Are there pet-friendly house rentals in Berwyn?
In Berwyn, there are several pet-friendly house rentals available, providing a welcoming environment for both travellers and their furry companions. Many of these properties feature amenities such as spacious backyards, which are superb for pets to roam, as well as modern kitchens and comfortable living areas. Some homes may also include additional conveniences like laundry facilities and off-street parking, suiting the needs of families or groups.The neighbourhood offers easy access to local parks, such as Proksa Park, where pets can enjoy fresh air and ample space to play. Additionally, the nearby Cermak Plaza provides a variety of shops and dining options, making it convenient for those with pets looking for pet-friendly cafes or services.
Are there any remote work holiday rentals in Berwyn?
In Berwyn, Illinois, there are numerous holiday rentals suitable for remote work, with around 128 options available. These accommodations typically offer amenities that cater to professionals, including free Wi-Fi, dedicated workspaces with desks and chairs, and generally reliable internet access. This makes it convenient for those looking to blend work and leisure while enjoying the local culture.The area itself is well-connected, with easy access to nearby attractions such as the charming shops and restaurants of the Historic Berwyn Arts District. Moreover, the proximity to Chicago allows for easy day trips to explore the vibrant city life, museums, and parks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Berwyn?
In Berwyn, popular rental amenities primarily include kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature a blender, ideal for making smoothies or other blended drinks. Onsite parking is commonly available, providing convenience for those travelling with vehicles. Additionally, holiday rentals often include coffee and tea makers, ensuring that guests can enjoy their morning brews at their leisure. Many accommodations also provide a desk, which is great for those needing a workspace during their visit.
When is the best time to visit Berwyn for a holiday rental?
The best time to visit Berwyn for a holiday rental is during the peak season from July to September. This vibrant period attracts a diverse crowd, including families and locals enjoying the warm weather and various outdoor events. July, in particular, stands out as the most popular month, offering a lively option superb for exploring local parks, attending community festivals, and enjoying the area's rich cultural offerings.During these summer months, you can expect pleasant temperatures ranging from the mid-teens to low 30s Celsius, making it ideal for outdoor activities like picnicking in the parks or strolling through the charming streets adorned with local art. The community comes alive with events, ensuring you have plenty of opportunities to engage with local culture and meet fellow travellers.For those seeking a more budget-friendly option, consider visiting in October. This month, while quieter, allows you to enjoy the beautiful autumn colours and the crispness of fall. It's a superb time for a more relaxed exploration of Berwyn's historical sites and local dining experiences, all while avoiding the summer crowds.
What are the top attractions in Berwyn?
In Berwyn, visitors can enjoy a range of attractions that reflect the city's unique character. The historic Depot District is a focal point, featuring charming shops and eateries, as well as the iconic Berwyn Route 66 sign, which pays homage to the famous highway. The area is also home to the Berwyn Cultural Centre, where various art exhibitions and community events take place.For outdoor enthusiasts, the beautiful Proksa Park offers walking trails, playgrounds, and picnic areas, providing a superb spot for relaxation. Additionally, the nearby Kollar Park features sports facilities and open green spaces, ideal for families and friends looking to enjoy some fresh air.Art lovers can explore the local art scene through the Berwyn Arts and Culture Council, which often hosts events and showcases local artists.
Are all fees included in the Berwyn 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 Berwyn holiday homes with parking?
Stayz offers a wide selection of holiday homes in Berwyn 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 Berwyn holiday homes?
You can find great discounts on holiday homes in Berwyn 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 Berwyn holiday home booking on Stayz?
To find Berwyn 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 Berwyn?
A long-stay holiday home in Berwyn 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 Berwyn holiday home?
Book your Berwyn 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 Berwyn?
Prices for holiday homes in Berwyn 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 Berwyn 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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