
Holiday houses in Berwyn
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Quick stats about holiday rentals in Berwyn

Total holiday rentals
Explore 110 holiday rentals in Berwyn

Nightly prices starting at
Berwyn holiday rentals start at $35 NZD per night before taxes and fees

Verified guest reviews
Over 7,450 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
110 of Berwyn holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Berwyn rentals

4.8 Average rating
Berwyn stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated holiday rentals in Berwyn
Guests agree: these stays are highly rated for location, cleanliness and more.

2 bedroom• 3 beds • 1 bath Apartment in Berwyn
Enjoy a stylish and elegant experience at this centrally-located private apartment On famous Route 66. Sunny, clutter free very spacious 2nd floor. Apt. Can sleep upto 6 ppl. Inflatable bed added for extra sleep option. Prepped for photo sessions of your own. •Restaurants, Auto repair shops and Walgreens are walking distance and much more. •Metra is a 10-15 minute walk. •DT Chicago 18 min •Brookfield Zoo 15 min Away •Midway Airport 15 min •O’Hare Airport 30 min •Mall 10 min •Loyola Hospital

Cozy & Peaceful Oasis Near City | 2BR + 1.5 Bath |
Unwind in this stylish 2-bedroom home in Berwyn just 20 mins from Downtown Chicago and Midway Airport. Berwyn is full of award-winning restaurants, bars, shops, & attractions. Adventure through Chicago from this prime location with ample street parking, accessible highways, and public transportation. Enjoy the private backyard during the summer months, relax on the hammock, and even grill a delicious meal! • Full Kitchen • 2 Bedrooms • Private Backyard • High-Speed Wi-Fi • Pool Table • 2 Levels

1 bedroom garden apartment in Forest Park
Unique private garden apartment in our single family residence. Approximately 8 miles directly west of downtown Chicago. Close to shopping, dining, entertainment and public transportation to the city. One bedroom & best for 2 people but could sleep 3 ($50 fee) for short stays. It's important to note that we have pets (cats/dog) in this home and also that this is a garden/ground/lower level apartment. The ceilings are relatively low at 6.5'. This would not be the best space for tall people.

Contemporary NEW Entire Suite Berwyn/Riverside
Welcome to your private oasis! This beautifully NEW appointed 1 bd unit offers the perfect blend of modern convenience and contemporary style. Whether you’re here for a weekend getaway or an extended stay, this contemporary retreat is your perfect home base. Explore the vibrant attractions of Berwyn or the excitement of Chicago, just a short trip away. Book today to secure your stay and experience the blend of comfort and style in this chic contemporary gem. We look forward to hosting you!

Oak Park cozy carriage house-lovely, walkable area
Our comfortable, stylish retreat has everything you need to relax and recharge. Whether you are visiting to explore all that beautiful Oak Park and downtown Chicago offer or desire a peaceful space to work. -> Quiet, walkable street near popular cafes, restaurants, taverns, parks, historic homes -> Steps from the "L" Blue Line Oak Park station -> Stocked w/ snacks + gourmet coffee/tea set-up (grinder, AeroPress, and Keurig) -> Onsite off-street parking -> A/C + heat -> garden sitting area

Private apartment with retro vibe
Cozy 1 BR apartment with retro touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus brand new twin sofa bed, + 1 more twin available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, great bakery. NO smoking, candles or glitter! (Yes, I truly needed to add the “no glitter” rule! (You can only imagine!)

RetroModern Bungalow | pet friendly | free parking
Experience the city in style at Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fenced-in, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location—just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage and/or catch the train a few blocks away.

Circle Back Modern Apartment
Sit on your leafy private patio and enjoy your coffee before heading out to the city- or wind down at the end of the day with a cold beer. Steps to coffee shops, neighborhood pubs, and the Blue Line train this beautifully updated and decorated apartment is the perfect landing pad for your Chicago adventure. FREE off-street parking, free in-unit laundry, a cute coffee station- basically every amenity we could think of! This will be the place you want to stay every time you visit Chicago.

Clean, Central Studio/ Urban Farm, Parking, for 4
Escape to an enchanting garden studio nestled in Oak Park's famous historic district. Discover our private urban farm with full gardens and 6 cheerful hens. Stroll to charming stores, cafes, and restaurants, or hop the nearby "L" for effortless Chicago adventures. Free parking, easy airport access. This serene, non-smoking studio with a kitchenette requires no check-out chores. No parties, 4 guests max. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Paradise in the Park
Welcome to our home. Enjoy the park connected to our backyard, featuring new playgrounds, soccer fields, and a walking trail. Our well-appointed kitchen is ideal for preparing meals together. The living areas provide plenty of space for bonding, and our extra comfy beds will ensure your maximum relaxation. We are located 20 minutes from the heart of Chicago, and about 10 minutes from Midway Airport, several hospitals, and the famous Brookfield Zoo. We can't wait to host you!

Cozy, Sunny, and Clean Apt 3 bd Free Parking
Relax in this stylish three-bedroom apartment in Berwyn located only 25 minutes from Downtown Chicago and 20 minutes from Midway Airport. Adventure through Chicago and the region easily from this prime location with ample street parking, accessible highways, and public transportation. Venture out to the local restaurants, bars, and nightlife. ✔ Beautiful and Comfortable Bedrooms ✔ 58” Smart TV in Living Room ✔ Full Kitchen ✔ Ample Street Parking ✔ High-Speed Wi-Fi

House to Relax
The whole group will enjoy easy access to everything from this centrally located place. Public transport is in front of the house, so you will get easy access to any place. Downtown Chicago is very close and shopping center is few blocks away. This place is quite big, super clean and you will have a lot space for all the family. In this place you'll find all the dishes to cook if you want. It's very close to supermarkets, restaurants and a lot different stores.
Popular amenities for Berwyn holiday rentals
Stay near Berwyn's top sights
Other great holiday rentals in Berwyn

Modern Condo • Pet Friendly • Walk to Train

A Pleasant Stay in Oak Park

Artful Abode: Cozy & Stylish Stay

Wonderful 1BR Retreat with Balcony in Oak Park

Cozy & Stylish Apt for 4 Near City+Airport

Where Comfort Begins - Unit 1

Cozy 2BR |Near Downtown Chicago Sleeps 7 +Parking

Cozy 1BR Near City + Airport
When is the best time to visit Berwyn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $156 NZD | $167 NZD | $177 NZD | $161 NZD | $202 NZD | $211 NZD | $227 NZD | $214 NZD | $195 NZD | $190 NZD | $174 NZD | $177 NZD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Frequently Asked Questions
What are the best places to stay in Berwyn?
Berwyn has family homes, cozy bungalows, and apartments suited for groups, solo travelers, and families. Staying near the Depot District can make it easy to explore local dining and shops in a vibrant neighborhood.
What are the best things to do in Berwyn with kids?
Families often enjoy playful afternoons at community parks, visiting local libraries for children’s activities, and attending seasonal cultural events around town. Art workshops and family-friendly cafés are also frequently suggested.
What are some of the best things to do in Berwyn?
Explore Berwyn’s Depot District for public art, dining, and shops, and enjoy local parks for outdoor relaxation. The city has vibrant community events and a growing arts scene worth experiencing.
How is the weather in Berwyn?
Berwyn has cold winters around 19–33°F (-7–0°C) and warm summers reaching 68–85°F (20–29°C). Pack layers for spring and autumn, which bring mild temperatures and occasional rain.
When is the best time to visit Berwyn?
Late spring through early autumn is often recommended for mild weather, outdoor activities, and local festivals. Winter is quieter, with chilly temperatures suited for indoor experiences.
What are the best places to visit in Berwyn?
Berwyn has vibrant public murals in the Depot District, community parks for relaxing outdoors, and a variety of galleries that highlight local creativity. The area is known for independent shops, neighborhood coffee spots, and historic architecture throughout the community.
What are some hiking trails in Berwyn?
Berwyn has walking paths in neighborhood parks for leisurely strolls, and wooded trails can be found in nearby forest preserves. Local residents often enjoy exploring these green spaces throughout the year.
What are some family activities we can do in Berwyn?
Explore playgrounds and community centers for hands-on activities, enjoy story hours at the Berwyn Public Library, and visit kid-friendly local eateries. Seasonal events invite families to connect with Berwyn’s welcoming community.
What are some of the best day trip ideas from Berwyn?
Many visitors explore nearby forest preserves for nature walks, visit museums in the surrounding area, or experience the vibrant city life of Chicago. Botanical gardens and historic neighborhoods around Berwyn are frequently suggested.
Are there any pet friendly accommodations available in Berwyn?
Berwyn has pet-friendly stays, especially in residential neighborhoods and private homes. Look for listings that welcome pets and provide easy access to parks for walks.
What are some local tips for visiting Berwyn?
Consider exploring Berwyn on foot to discover public murals and independent shops in the Depot District. Local farmers’ markets and street festivals are a great way to experience the area’s community vibe.
What is Berwyn known for?
Berwyn is known for its historic Route 66 ties, lively Depot District, and a tradition of community events. Public art and mid-century architecture add distinctive character to the city’s landscape.
What are the best hidden gems to explore in Berwyn?
Discover smaller art galleries, quirky vintage shops, and locally owned cafés tucked around the Depot District. The city’s public murals and community theater performances are also frequently suggested for visitors looking for unique experiences.
What are the best foods to try in Berwyn?
Berwyn has locally rooted flavors including classic Chicago-style pizza, diverse Latin American and Eastern European dishes, and casual diners serving community favorites. Bakeries in town are known for sweet pastries and fresh bread.
What should I bring for a trip to Berwyn?
Pack comfortable walking shoes for exploring neighborhoods, layers for variable temperatures, and rain gear in spring and autumn. Having a reusable water bottle and sun protection is also often recommended.
What is the nightlife in Berwyn like?
Berwyn has laid-back lounges, locally owned bars, and venues hosting live bands or community performances. The Depot District is known for its vibrant nightlife scene with casual eateries and music events.
What are the most popular events or festivals in Berwyn?
Berwyn hosts music festivals, art fairs, and community parades, often centered around the Depot District and public parks. Summer block parties and seasonal celebrations draw neighbors and visitors together throughout the year.
Are there family friendly vacation rentals in Berwyn?
Berwyn has vacation rentals suited for families, such as spacious homes and apartments near parks and playgrounds. Many hosts provide amenities like full kitchens and child-friendly spaces to make group stays comfortable.
Destinations to explore
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- Wrigley Field
- Lincoln Park
- United Center
- Soldier Field
- Grant Park
- Navy Pier
- Millennium Park
- 875 North Michigan Avenue
- Naval Station Great Lakes
- Indiana Dunes State Park
- Six Flags Great America
- Shedd Aquarium
- The Field Museum
- Humboldt Park
- Chicago River Walk
- University of Chicago
- SeatGeek Stadium
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Frank Lloyd Wright Home and Studio
- Union Park
- Donald E Stephens Convention Center
- Wilmot Mountain Ski Resort





