Holiday houses in Berwyn

4.91 out of 5 average rating, 384 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.

4.85 out of 5 average rating, 102 reviews

Guest suite in Berwyn

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"

4.97 out of 5 average rating, 311 reviews

Apartment in Cicero

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

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

Top Guest favourite

Home in Berwyn

4.99 out of 5 average rating, 146 reviews

Retro Modern Bungalow | fire pit | free parking

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] back yard. Enjoy central HVAC, hi-speed 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.

Superhost

4.84 out of 5 average rating, 103 reviews

Bright & Gorgeous- 5* Location- Queen Beds - Pkg

Leave your worries behind at this peaceful, secure retreat with plenty of space to relax. 2nd-floor duplex to 3rd floor. Just a 15-minute drive to/from downtown. Easily walk to everything: - Groceries, sushi, coffee shop, brewery - Nightlife, live music, and great food - Playgrounds, parks, public pool, & tennis courts Enjoy all the comforts of home in a charming, urban-suburban mix. - Only 1.5 blocks to the Oak Park Av. CTA "L" Blue Line stop & I-290 Housebroken dogs welcome.

4.86 out of 5 average rating, 292 reviews

Cozy and Character-Rich Chicago Style, Tv NFL PASS

→ 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

Superhost

4.82 out of 5 average rating, 123 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.

4.9 out of 5 average rating, 304 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.

4.92 out of 5 average rating, 106 reviews

Condo in Berwyn

3 Bed Vintage Condo In Chicagolands Trendy Berwyn

Start your adventures in this lovely three-bedroom hidden gem in Berwyn, just minutes away from Chicago and everything the city has to offer. Enjoy an abundance of natural light and comfort featuring three charming bedrooms, one bath, streaming TV, and several other amenities. Perfect for six guests, the location is steps away from the Roosevelt bus stop and a ten-minute walk to the Blue line, which will take you to world-class museums, the lakefront, the Magnificent Mile and more.

4.97 out of 5 average rating, 116 reviews

Home in Oak Park

Garden Unit, King & Queen, Kitchenette & Parking

Our comfy, recently remodeled garden unit is 3 blocks to the train with free parking in upscale, safe, walkable Oak Park. Enjoy some time in our little urban farm. Check out the gardens and visit our 4 friendly hens. This non-smoking studio with a kitchenette is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties, 4 guests max allowed. Minimum age to book is 25. Visit my profile for additional units

Top Guest favourite

4.98 out of 5 average rating, 200 reviews

Modern+Spacious W/King Bed, Walk to Town-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 We kindly ask that you read our full listing description and our house rules prior to booking. 4 guests maximum-no visitors allowed

4.95 out of 5 average rating, 227 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.

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Other great holiday rentals in Berwyn

4.94 out of 5 average rating, 305 reviews

Private room in Oak Park

Single bedroom with Asian decor in family home

MichaelRating, 5 stars5 days ago

A very nice house close to the metro and in a peaceful suburb. John and Daniel was very welcoming hosts and gave me helpful hints on places to eat in the local area.

4.78 out of 5 average rating, 74 reviews

Cozy & Private 1 BR Near City + Airports

DanielRating, 5 stars2 weeks ago

Super clean place really enjoyed my stay.bathroom a little small but overall everything was as expected as he described really nice would definitely stay again.

Top Guest favourite

Private room in Berwyn

4.97 out of 5 average rating, 124 reviews

Private lower level suite suburb Chicago

JasmineRating, 5 stars1 week ago

Aurora was an amazing host. We had just stayed one night because we were just in town for a WNBA game. the arena was close to the house, which was nice. I loved how close she lived to the city but also far enough that the neighborhood was quiet. In the morning when we woke up Aurora had gave us nice suggestions for breakfast and it was a really good restaurant. Aurora was also super helpful when I needed help with the TV because it wouldn’t turn on and she came right down to fix it! She also had water and snacks laid out for us, which was also very nice and comforting.

Superhost

Private room in Berwyn

4.87 out of 5 average rating, 55 reviews

The Quilt Room. Micro-flower farm.

TaliahRating, 5 stars2 weeks ago

The home was perfect for our trip to chicago! We will definitely come back again

Home in Berwyn

5 out of 5 average rating, 3 reviews

Spacious Historic Bungalow

CesarRating, 5 stars3 days ago

Juan was extremely nice and very communicative. We truly had a great time at his home and would love to rent it again

Private room in North Riverside

4.93 out of 5 average rating, 215 reviews

The Albany Park Room at the Cape Cod in Riverside

GianfrancoRating, 5 stars1 week ago

I had an amazing experience staying at this Airbnb! From the moment I arrived, everything exceeded my expectations. The space was spotless, beautifully decorated, and exactly as described—if not better. The bed was incredibly comfortable, and all the little touches (like fresh towels and local recommendations) made it feel like a home away from home. The host was outstanding—friendly, responsive, and genuinely committed to making sure I had a great stay. Check-in and check-out were seamless, and they went above and beyond to accommodate any questions I had. The location was perfect: quiet and peaceful, but still close to restaurants, shops, and everything I wanted to explore. Whether you’re traveling for business or a getaway, I highly recommend this place. I’ll definitely be coming back!