Vacation rentals in Berwyn

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Top-rated vacation rentals in Berwyn

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost
A modern living area features a sleek black sofa paired with two cozy white armchairs. Natural light pours in through large windows adorned with light grey curtains. Minimalist decor includes two framed artworks and a small wooden side table that complements the space.
Apartment in Berwyn
4.85 out of 5 average rating, 151 reviews

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

Guest favorite
A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.
Home in Berwyn
4.98 out of 5 average rating, 202 reviews

RetroModern Bungalow | free parking | pet friendly

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 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.

Guest favorite
A cozy living area features a gray sofa and a blue armchair, complemented by decorative cushions. A wooden coffee table sits on a patterned rug, with a laptop placed on top. Natural light filters through the window, enhancing the inviting space.
Apartment in Oak Park
4.85 out of 5 average rating, 210 reviews

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.

Superhost
The living room features a spacious teal sofa paired with a simple black coffee table in front. A window with sheer curtains allows natural light to fill the area, complemented by a floor lamp and potted plants. Hardwood floors add warmth to the room.
Apartment in Berwyn
4.89 out of 5 average rating, 394 reviews

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.

Top guest favorite
A charming house is framed by a lush garden filled with various shrubs and flowering plants. The exterior features a mix of wood siding and prominent windows, while a white picket fence lines the front yard, enhancing the home's inviting presence.
Guest suite in Oak Park
4.91 out of 5 average rating, 521 reviews

Entire upstairs in Arts and Crafts Oak Park home

You have the use of the entire upstairs (with a separate, lockable private entrance). With two bedrooms, bathroom and a common area with a futon, fridge, microwave, coffee maker and kettle, it is flexible for individuals or small groups of no more than 4 people. Free overnight parking. We're a quick walk to the CTA Blue line, coffee shops and restaurants, parks, musical venues, the Oak Park Arts District, and a quick drive to downtown. Our home is cozy, in a friendly neighborhood.

Top guest favorite
The exterior of a two-story house is shown, featuring a dark grey facade with white trim. Large windows are adorned with flower boxes displaying colorful blooms. Steps lead to a covered porch, inviting entry into the home.
Apartment in Oak Park
4.89 out of 5 average rating, 184 reviews

A Little Slice of Heaven in Oak Park, IL

A private space with a fun vintage vibe. Located several blocks from the El and the Eisenhower, it’s really easy to access the city. It also includes free off-street parking which is a must. The space is located in my basement and has a private entrance. I do live in the house above so you will hear some noises including my dog - but we do try to be quiet. The space includes a bedroom, spacious living area and an updated bathroom. Please contact me with any questions

Guest favorite
A vibrant cityscape of downtown Chicago is captured at dusk, showcasing towering buildings including the Willis Tower. The scene is highlighted by a bridge over a river, with colorful hues in the sky reflecting pink and purple tones.
Home in Berwyn
4.92 out of 5 average rating, 154 reviews

Beautiful Bungalow, Near Downtown Chicago

Beautiful, cozy, vintage home in a centrally located quiet neighborhood. Close to downtown Chicago, O'Hare and Midway Airports as well as many attractions, museums and great places to eat. This home includes High Speed Wifi, Full Kitchen, Full washer/dryer, tv's with streaming and a game loft full of board games and game consoles for all guests to enjoy. Contactless check-in and check-out with keyless entry. 3 Bedrooms, 4 queen beds, 1.5 baths. Sleeps 8 guests total.

Top guest favorite
A bright kitchen area features a round table with a red and white checkered tablecloth and four white chairs. A small sink and a gas stove are present, along with a refrigerator. Natural light filters through a window adorned with a red gingham curtain.
Apartment in Berwyn
4.92 out of 5 average rating, 490 reviews

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! Pets MUST be pre-approved and never left

Top guest favorite
A bright living area features a brown sofa adorned with a green accent pillow, positioned in front of a simple black coffee table. Natural light enters through multiple windows, illuminating the space. Decorative wall art and a unique mirror enhance the inviting atmosphere.
Apartment in Oak Park
4.98 out of 5 average rating, 362 reviews

Bright & Spacious Victorian-FREE PKG walk to train

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Walk to all tourist attractions, public transportation that takes you directly to downtown Chicago, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago. We kindly ask that you read our full listing description and our house rules prior to booking.

Top guest favorite
A bright living room is depicted, featuring a spacious sofa adorned with decorative pillows. A large flat-screen TV is positioned across from a glass coffee table, while natural light flows through tall windows framed by light curtains. Indoor plants add a touch of greenery to the space.
Apartment in Berwyn
4.95 out of 5 average rating, 303 reviews

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.

Top guest favorite
An inviting living area features a white couch paired with a dark coffee table, facing a flat-screen TV. The modern kitchen showcases sleek cabinetry, a stainless steel refrigerator, and a central island with bar seating, lit by overhead lighting.
Guesthouse in Oak Park
4.89 out of 5 average rating, 546 reviews

Coachhouse in central OP 4 blk to L

Just updated, furnished 1 BR 1 BA apt in Frank Lloyd Wright Historic District. Parking, kitchen, washer/dryer in unit, Air/Heat, Smart TV. Free wifi. Central location: 1 blk to farmers market, near Hemingway / Frank Lloyd Wright attractions. 4 blocks to green line. 20 min ride to downtown Chicago. Available for longer term stays.

Top guest favorite
Guesthouse in Oak Park
4.94 out of 5 average rating, 130 reviews

O'Malley Oasis!

Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!

Popular amenities for Berwyn places to stay

When is the best time to visit Berwyn?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$16,945 GYDG$17,991 GYDG$18,619 GYDG$19,037 GYDG$23,849 GYDG$24,895 GYDG$26,778 GYDG$25,313 GYDG$23,012 GYDG$22,385 GYDG$20,502 GYDG$20,920 GYD
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°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 vacation rentals in Berwyn

  • Total vacation rentals

    Explore 110 vacation rentals in Berwyn

  • Nightly prices starting at

    Berwyn vacation rentals start at G$4,184 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,450 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Berwyn vacation 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!

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