
Holiday rentals in Berwyn
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Top-rated holiday rentals in Berwyn
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Best Place to Rest, near Chicago
Unit with private entrance, close to Berwyn's restaurants, bars, shops, and entertainment. Close to public transportation via the Metra Train Station, Pace Buses, and near the CTA Pink [1.5 miles], Blue [2.3 miles], and Green [3.4 miles] Train lines. Near Oak Park, North Riverside, and Chicago. This is an awesome location. There is parking on the street (A street pass is required and will be provided each day). The unit is 185 sq ft located in the basement with 4 stairs, ceiling height is 6' 6"

City-Accessible Basement Retreat
Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Chicago-Style, Vintage, Cable & NFL PASS 42-1
→ Introducing our newly renovated and furnished apartment unit nestled in the charming Oak Park Art District. Experience vintage Chicago style living in this richly characteristic brick building, situated in a safe and quiet neighborhood. ★ Property Features: • One block away from the Oak Park Art District • Vintage Chicago style brick building • Safe, quiet neighborhood • Newly renovated and furnished • Smart TV with Cable and option to use other apps • Free Laundry Room • Free Parking

Retro Modern Bungalow | free parking | fire pit
Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, 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 or catch the train a few blocks away.

The Green Bungalow: Charming 1-BR apt. with patio
Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Walking Distance to Everything.
This apartment is available for 1 year lease. $2400 a month fully furnished, available March 1st. The Green Line CTA "L" train is only 3 blocks away and departs every 10 minutes. Metra shares a station and departs once an hour. Freight trains also pass by. You will hear these trains train throughout the night. Most people are not disturbed by this sound. If you are a light sleeper I recommend earplugs for sleeping. Taxi from the Airport, around $80. Neighborhood parking is limited.

Private apartment with retro vibe
December discount dates! 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! Pets MUST be pre-approved and never left

Comfy Studio in Walkable Area w/ 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.

The Cosmopolitan Unit
Feel like you traveled all around the world by visiting our Cosmopolitan Unit. Each bedroom is inspired by different city from all around the globe. 3 bedroom apartment with fully equipped kitchen. Fast wi-fi and TV in each bedroom. For those who enjoy working out while on vacation, we even have a Peloton bike. This second floor apartment is located within 15-20 min drive from downtown Chicago. Public transportation and restaurants within walking distance.

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 space. 2nd Floor Apt. can sleep upto 6 people. Inflatable bed added as an 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 is approximately 18 min from your stay. •Brookfield Zoo 15 min Away

2 Bed Apartment | Convenient Access to Downtown
Enjoy your stay in Forest Park in this modern, newly remodeled two-bedroom apartment in first level of the 3 unit building! It is conveniently located close right by highway ,dependent on the traffic, without traffic drive just 20 minutes to Chicago downtown. O’Hare and Midway Airports 30minutes a way. The apartment is comfortable for up 4 people, has a two private bedrooms with queen beds and a pull out sofa in the living room.

Spacious Oasis Berwyn with Free Parking
Welcome to Spacious Oasis Berwyn! Make your stay in the area easy. Take advantage of our centralized location where most destinations are only 20 minutes away by car and public transit is less than a block away. Great food, parks, nightlife, and shopping are all within walking distance. Whatever brings you to "My Kind of Town", our oasis is sure to please with ease.
Popular amenities for Berwyn holiday rentals
Stay near Berwyn's top sights
Other great holiday rentals in Berwyn

Single bedroom with Asian decor in family home

A1- Next to the train & Downtown

Private lower level suite suburb Chicago

Private Parking, Comfy Bed

Antique Filled Home

Room T3

Chi-Town Hideout #3

Walk to Train | Master Suite A Queen Bed Sleeps 2
When is the best time to visit Berwyn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £60 | £64 | £66 | £68 | £85 | £89 | £95 | £90 | £82 | £76 | £70 | £67 |
| 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.
Quick stats about holiday rentals in Berwyn

Total holiday rentals
Explore 120 holiday rentals in Berwyn

Nightly prices starting at
Berwyn holiday rentals start at £7 per night before taxes and fees

Verified guest reviews
Over 7,050 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
110 of Berwyn holiday rentals include wifi 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!
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