Berwyn holiday rentals

We found 2,837 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:11 Dec - 18 Dec

Room
Interior
Exterior
Terrace/patio
Exceptional
(39 reviews)

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

Chicago

8% off
AU$34,309
for 7 nights, 1 home
AU$4,901 per night
includes taxes & fees
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
The building
River North Luxury Living
Outdoors at night
French Bistro and Wine Bar - right downstairs
Exceptional
(105 reviews)

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

Chicago

7% off
AU$4,567
for 7 nights, 1 apartment
AU$652 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Room
Cozy Home
Interior
Private kitchen
Exceptional
(12 reviews)

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

Chicago

7% off
AU$4,838
for 7 nights, 1 home
AU$691 per night
includes taxes & fees
Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking
Dining
Interior
Private kitchen
Room
Exceptional
(40 reviews)

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

Berwyn

8% off
AU$1,687
for 7 nights, 1 apartment
AU$241 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Dining
Exterior
Interior
Private kitchen
Exceptional
(25 reviews)

Beautiful Berwyn Bungalow Close to Downtown Chicago

Berwyn

8% off
AU$3,447
for 7 nights, 1 home
AU$492 per night
includes taxes & fees
Beautiful Berwyn Bungalow Close to Downtown Chicago
Exterior
Private kitchen
Interior
Interior
Exceptional
(27 reviews)

Stunning 6 BR Home * Chicago * Centrally Located

Chicago

7% off
AU$4,299
for 7 nights, 1 home
AU$614 per night
includes taxes & fees
Stunning 6 BR Home * Chicago * Centrally Located
Bedroom 1 - King Bed
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$7,942
for 7 nights, 1 home
AU$1,135 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Front Yard View
Living Room
Kitchen
Bedroom 1 (King Size) + 55Inch TV
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$5,412
for 7 nights, 1 home
AU$773 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Living area
Dining
Private kitchen
Living area
Exceptional
(15 reviews)

Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks

Burr Ridge

8% off
AU$5,411
for 7 nights, 1 home
AU$773 per night
includes taxes & fees
Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Living room area opens into dining room & kitchen
Living room area
Exceptional
(99 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
AU$6,329
for 7 nights, 1 home
AU$904 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Exterior
Private kitchen
Living area
Bedroom 1
Wonderful
(22 reviews)

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Chicago

7% off
AU$6,405
for 7 nights, 1 home
AU$915 per night
includes taxes & fees
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Interior
Living area
Room
Dining
Exceptional
(22 reviews)

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

Berwyn

8% off
AU$1,405
for 7 nights, 1 apartment
AU$201 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Dining
Living area
Terrace/patio
Living area
Exceptional
(56 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$3,648
for 7 nights, 1 apartment
AU$521 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Room
Interior
Dining
Living area
Exceptional
(38 reviews)

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago

7% off
AU$5,916
for 7 nights, 1 home
AU$845 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Living area
Interior
Private kitchen
Interior
Wonderful
(87 reviews)

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

Chicago

5% off
AU$1,199
for 7 nights, 1 apartment
AU$171 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Point of interest
Living area
Miscellaneous
Room
Exceptional
(15 reviews)

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

11% off
AU$4,858
for 7 nights, 1 home
AU$694 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Private kitchen
Interior
Living area
Room
Exceptional
(12 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
AU$2,977
for 7 nights, 1 apartment
AU$425 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Upstairs queen bedroom 2
Downstairs living area
Kitchen (upstairs)
Fun Mirror Wall Upstairs
Exceptional
(99 reviews)

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

Chicago

7% off
AU$12,331
for 7 nights, 1 apartment
AU$1,762 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Living area
Interior
Room
Living area
Exceptional
(24 reviews)

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

Berwyn

8% off
AU$1,372
for 7 nights, 1 apartment
AU$196 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Private kitchen
Living area
Interior
Room
Exceptional
(7 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
AU$4,450
for 7 nights, 1 apartment
AU$636 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Private kitchen
Living area
Room
Interior detail
Exceptional
(14 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$2,061
for 7 nights, 1 apartment
AU$294 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Interior
Interior
Dining
Private kitchen
Exceptional
(17 reviews)

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

Chicago

6% off
AU$1,674
for 7 nights, 1 apartment
AU$239 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Living area
Dining
Private kitchen
Living area
Wonderful
(20 reviews)

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

Berwyn

8% off
AU$1,415
for 7 nights, 1 apartment
AU$202 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Bedroom #1 w 2 full size beds plus a desk
Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc
Private kitchen
7 minutes drive to downtown and Millenium Park
Wonderful
(25 reviews)

1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
AU$2,689
for 7 nights, 1 apartment
AU$384 per night
includes taxes & fees
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

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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:

  • 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)
  • Rainbow Falls Waterpark (15 mi / 24.2 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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