Holiday houses in Berwyn

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Top-rated holiday rentals in Berwyn

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Guest favourite

Home in Berwyn

4.92 out of 5 average rating, 237 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed 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, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

5 – 12 Sept

$1,222 AUD total

Guest favourite

Guest suite in Oak Park

4.89 out of 5 average rating, 399 reviews

Entire upstairs in Arts and Crafts Oak Park home

You have the use of the entire upstairs (with a separate, lockable private entrance) and bicycles. With two bedrooms, bathroom and a common area with a futon, table, fridge, microwave, coffee maker and kettle, it is flexible for individuals, couples, families or small groups. 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.

25 Dec – 1 Jan

$1,494 AUD total

Guest favourite

Apartment in Oak Park

4.85 out of 5 average rating, 527 reviews

Long stays welcome@warm&cute vintage 2BR

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

2 – 9 Oct

$1,349 AUD total

Guest favourite

Apartment in Berwyn

4.92 out of 5 average rating, 148 reviews

Friendly Rock ’n’ Roll Retreat

Get creative in this music-inspired getaway above the iconic Friendly Music Community. Co-hosted by the 2021 #1 Top Host in Illinois. Explore the many instruments in the funky retreat, enjoy local live music in the bar, relax in the Coffee Lounge, take a music lesson at the Friendly Music School. Nearby: Frank Lloyd Wright Home/Studio, Birthplace of Ernest Hemingway, easy train to downtown Chicago and Mag Mile.

3 – 10 Nov

$1,391 AUD total

Guest favourite

Apartment in Berwyn

4.87 out of 5 average rating, 136 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.

11 – 18 July

$1,303 AUD total

Guest favourite

Apartment in Berwyn

4.99 out of 5 average rating, 251 reviews

Berwyn Betty Apartment

New to the market- this completely renovated apartment sits atop our Bath and Body workshop. Our small business began in our home 8 years ago and in 2016 it became too big to stay there. We bought this run down corner store building that sits on a double lot on a neighborhood street in south Berwyn. Over the next year, we completely renovated the building. The first floor is the home to our e-commerce business. The second floor was built with the traveller's needs in mind.

15 – 22 Jan

$2,047 AUD total

Superhost

Apartment in Berwyn

4.88 out of 5 average rating, 113 reviews

2 bd/1 bth Berwyn Apt 20 mins frm Chgo

Beautiful, spacious, 2 bedroom apartment with a dazzling fully stocked eat in kitchen and complimentary coffee bar. Relax in luxurious theater seats while enjoying the view from this second floor apartment. Located about 20 minutes outside Chicago. Just blocks away from a shopping mall, Metra train station, award-winning restaurants, bars, shops, and other amenities. This is a prime location. Book with us once you are ready to relax and retreat at our comfy second floor apt.

7 – 14 July

$2,136 AUD total

Guest favourite

Apartment in Forest Park

4.99 out of 5 average rating, 185 reviews

Walk to Oak Park from this Newly Remodeled Gem

This is an open, bright and comfortable home that has been fully renovated, but still has the historic charm of an older house (early 1900s). With a completely updated kitchen you have everything you need to fix a good meal or you can choose to eat out at one of the many restaurants and bars/brew pubs within close proximity. The apartment has an office nook with a desk and chair for getting your work done, or you can kick back and relax in the living and dining spaces.

27 Oct – 3 Nov

$1,593 AUD total

Guest favourite

Apartment in Cicero

4.98 out of 5 average rating, 200 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

24 Feb – 3 Mar

$1,539 AUD total

Guest favourite

Apartment in Forest Park

5.0 out of 5 average rating, 216 reviews

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park (with "The Mayberriest Downtown!"- Chicago Magazine), right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

4 – 11 Sept

$1,460 AUD total

Guest favourite

Apartment in Forest Park

4.84 out of 5 average rating, 109 reviews

Home away from home downstairs

Enjoy a stylish experience at this centrally-located, easy access , ground floor apartment. You will have a fully equipped kitchen, laundry facility outside your back door and super fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation.

6 – 13 Nov

$1,388 AUD total

Guest favourite

Apartment in Oak Park

4.87 out of 5 average rating, 127 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. The space includes a bedroom, living area and a bathroom. Space is great if you are in town to work or for fun! Please contact me with any questions.

19 – 26 Jan

$1,237 AUD total