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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Guest favorite
Apartment in Oak Park
4.84 out of 5 average rating, 232 reviews

Betty BnB

Free admission to The World's Smallest Betty White Museum! Oh, and a comfortable king-sized bed in a newly updated studio apartment. Centrally located in Oak Park, close to cafes and transit. Quiet, friendly neighborhood with ample street parking and a pub across the street. This is a basement unit with a kitchenette (NO STOVE/OVEN), cozy TV room, desk nook, and full bathroom. The bed is king-sized and has a firm mattress. The floors slope and there's no thermostat, but it's cute + welcoming

Top 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, 178 reviews

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at our 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.

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
4.91 out of 5 average rating, 448 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy 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 alone.

Guest favorite
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
4.9 out of 5 average rating, 361 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
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, 177 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

Top guest favorite
A cozy bedroom is visible through an open doorway, featuring a king size bed with decorative pillows and a soft blanket. Three framed wall decorations are arranged above the headboard, while bedside lamps provide soft illumination, creating a restful and inviting atmosphere.
Apartment in Oak Park
4.98 out of 5 average rating, 124 reviews

Cheerful Oak Park Apartment

Welcome to our lovely space, located above a unique piano restoration shop. Spacious and relaxing, with plenty to enjoy staying in, and 5-minutes walking distance to cafes, grocery, bars, restaurants, and more. The apartment is down the street from a Botanic Garden, and there is a nice arts district nearby. Easily accessible to downtown Oak Park and Chicago with nearby public transportation and expressway (downtown Chicago is about 25-35 min. drive, 35-45 min. by train).

Top guest favorite
Townhouse in Oak Park
4.94 out of 5 average rating, 123 reviews

Downtown Oak Park - Luxury 3 bed 3.5 bath Townhome

Entire townhome located in charming downtown Oak Park. Luxury accommodations. Free Parking. Dog friendly. Highly-walkable area. Attached two-car garage. Chicago's El and Metra train stops a short 2-block walk. Both trains bring you to the heart of downtown with the El extending into many Chicago neighborhoods. Shopping, restaurants, Target, Trader Joe's and Frank Lloyd Wright homes within walking distance. TVs logged into Hulu, Disney +, ESPN, Netflix and HBO Max.

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
4.91 out of 5 average rating, 148 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.

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
4.83 out of 5 average rating, 109 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 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

Top guest favorite
A historic Queen Anne home features a distinctive turret and a wraparound porch, surrounded by lush greenery. The exterior showcases a blend of siding and masonry with intricate architectural details reflective of its 1889 origins.
Apartment in Oak Park
4.98 out of 5 average rating, 238 reviews

Chic Retreat in Historic Victorian House-Park Free

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Centrally located and within walking distance to all tourist attractions, public transportation, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago Perfect for long-term stays. 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, 278 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 open living area is highlighted by a spacious dark sofa adorned with decorative cushions, complemented by a wood coffee table. A large, comfortable bed occupies one side, while a dining area with a glass table and chairs is visible. Art pieces are displayed on the walls.
Guesthouse in Oak Park
4.99 out of 5 average rating, 134 reviews

Stylish Coachhouse in lovely Oak Park!

Enjoy the privacy and artistry of your very own coachhouse. The interior is a personalized mix of artistic, industrial and farmhouse. Cool colors, personalized details and local art included. You have your own washer, dryer, complete kitchen, and private patio space. Walk the lovely neighborhood, to the L train, or even to a local brewery.

Popular amenities for Berwyn places to stay

When is the best time to visit Berwyn?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,389 ZARR1,475 ZARR1,527 ZARR1,561 ZARR1,955 ZARR2,041 ZARR2,196 ZARR2,075 ZARR1,887 ZARR1,750 ZARR1,612 ZARR1,544 ZAR
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C

Frequently Asked Questions

  • Are there house rentals with a dedicated workspace in Berwyn?

    Yes! Work meets play with ease at over 20 house rentals in Berwyn featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Berwyn?

    Experience the best of Berwyn with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Berwyn have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Berwyn. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Berwyn have wifi?

    Absolutely! We offer over 60 apartment rentals with wifi in Berwyn. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly apartment rentals in Berwyn?

    Four-legged friends are welcome in Berwyn. Choose from more than 10 apartment rentals for guests traveling with pets.

  • What are the most popular amenities for House Rentals in Berwyn?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Berwyn

  • Total vacation rentals

    Explore 120 vacation rentals in Berwyn

  • Nightly prices starting at

    Berwyn vacation rentals start at R172 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 7,050 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 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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