Vacation rentals in Berwyn

4.83 out of 5 average rating, 206 reviews

2bdrm, WiFi, WFH, W&D, parking, central location

Chicago has been voted Best Big City in the U.S. by for a historic 6 years in a row! Our space offers things like fast wifi, a comfortable workspace, and/or is suitable for children, our cleaning lady is immaculate. This is a Spacious, LARGE 2 bedroom 1 bathroom unit with assigned parking space, in the heart of Berwyn and in a safe multicultural neighborhood. Snacks, water, soft drinks and coffee. THIS APARTMENT has been professionally painted and has newer Close to Costco, markets and takeout.

A book titled 'Haunts of the White City' is displayed against a dark surface. The cover features a vintage-style house and a large moon, with the title and subtitle prominently shown in a contrasting font. The overall color scheme emphasizes a mysterious and historical theme.

4.92 out of 5 average rating, 381 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, 101 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"

4.86 out of 5 average rating, 117 reviews

A modern kitchen area features white cabinetry and a sleek black refrigerator, complemented by stainless steel appliances. A round wooden dining table is set with four gray chairs. Exposed wooden beams enhance the open ceiling, illuminated by pendant lighting.

Apartment in Forest Park

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!

Superhost

A staircase features wooden steps leading upwards, illuminated by natural light. The walls are painted in a soft tone, creating a bright and inviting ascent. The wooden trim adds warmth to the space, completing the functional and welcoming design.

4.84 out of 5 average rating, 102 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.

Top guest favorite

The living room features mid-century furnishings, including a green velvet sofa and modern accent chairs. Natural light floods the space through large windows, highlighting a wooden accent wall and a decorative gallery of frames. A sleek coffee table sits in the center, creating a relaxed atmosphere.

Home in Berwyn

4.99 out of 5 average rating, 145 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

A modern kitchen is shown, featuring gray cabinets and a granite countertop. A microwave sits on the counter beside a double sink. Wooden cutting boards and a bowl with a small plant are arranged neatly in the background against a white tiled backsplash.

4.82 out of 5 average rating, 122 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.

The exterior view of a vintage bungalow is captured, showcasing its brick façade and welcoming entryway. Green shrubs flank the front steps, while a flag adorns the porch. A spacious lawn is visible, and neighboring houses create a sense of a residential neighborhood.

4.9 out of 5 average rating, 301 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.

A spacious living area is highlighted by a large TV setup and a comfortable red accent chair. The floor features a plush rug, while walls are adorned with framed artwork. Various seating options and a workstation are available, enhancing the versatility of the space.

4.89 out of 5 average rating, 162 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

The historic Queen Anne home features a distinctive turret and spacious front porch. The exterior showcases a harmonious blend of light-colored siding and intricate detailing. Lush greenery and landscaped areas surround the house, creating an inviting setting for guests.

4.97 out of 5 average rating, 199 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

A stylish room divider with a decorative design separates two living spaces. The cozy sitting area features a plush sofa and a large window adorned with sheer curtains. A vibrant plant adds a touch of greenery, and natural light illuminates the warm wooden floors.

4.95 out of 5 average rating, 226 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.

4.9 out of 5 average rating, 126 reviews

A brick two-story apartment building is situated among well-maintained greenery. Large windows are visible on the front facade, allowing natural light to enter. The residential neighborhood features a mix of similarly styled homes, highlighting the inviting character of the area.

Condo in Berwyn

Picturesque Apartment in Berwyn

This stylish place to stay is perfect for group trips. 2 bedrooms with queen beds, spacious living room with a sofa bed and well equipped kitchen. The apartment is located in North Berwyn, 15 minutes drive from Downtown Chicago, walking distance to Roosevelt Road's bars and restaurants, 0.8 miles to CTA Blue Line rail line station.

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Popular amenities for Berwyn vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Berwyn

Top guest favorite

The exterior of a modern three-story bungalow is showcased, featuring a mix of brick and dark paneling. A neatly landscaped front yard includes a path leading to the entryway, flanked by lush greenery and decorative stones. The structure retains a contemporary architectural style.

Home in Berwyn

5 out of 5 average rating, 12 reviews

The Architectural Haven - 15 min from Chicago!

4.78 out of 5 average rating, 73 reviews

Cozy & Private 1 BR Near City + Airports

4.88 out of 5 average rating, 16 reviews

A spacious living area features a navy blue sectional sofa paired with a round white coffee table. Soft textures are added by a knitted red throw draped over the sofa. Potted plants stand by the walls, contributing to a refreshing ambiance.

Home in Berwyn

Modern and Clean Comfort

A modern kitchen showcases rich wooden cabinetry and stainless steel appliances. A round dining table, surrounded by four black chairs, sits on a textured, light-colored area rug. Bright overhead lights illuminate the space, while a staircase leads to the upper level.

4.91 out of 5 average rating, 92 reviews

Renovated Berwyn Apartment with Vintage Style

A fully equipped kitchen corner features a modern coffee maker and a classic drip coffee machine, both placed on a textured granite countertop. Glass storage jars are visible on the countertop, alongside gray cabinetry that adds a contemporary touch.

4.87 out of 5 average rating, 45 reviews

Serene Suburban Stay: Family-Friendly w/EZ Parking

A tandem bicycle is positioned in front of the Friendly Community Room, showcasing a blue frame with yellow accents. The cafe's large window displays the name and a striking piece of art inside, with reflections of passersby visible on the glass.

4.88 out of 5 average rating, 194 reviews

Friendly Rock ’n’ Roll Retreat

Private room in North Riverside

An inviting shared area features a bar with four stools, a television on a low wooden stand, and a cozy rug on the floor. A plant adds a touch of greenery, while natural light filters through a nearby window above the bar.

4.93 out of 5 average rating, 214 reviews

The Albany Park Room at the Cape Cod in Riverside

A panoramic view of a vibrant city skyline at dusk, featuring tall buildings illuminated with warm lights. The orange and purple hues of the sunset reflect on the river, while streaks of headlights from moving vehicles create a sense of motion along the waterfront.