Family-friendly vacation rentals in Berwyn

4.83 out of 5 average rating, 111 reviews

A living room is presented with light-colored walls and hardwood flooring. Comfortable seating arrangements include two light armchairs and a grey sofa with decorative pillows. A round coffee table sits in the center, complemented by a chic area rug. Natural light enters through two windows, enhancing the bright atmosphere.

Apartment in Berwyn

House to Relax

Elegant/Spacious 2bd Apt close to Chicago Stay includes: * 1 Free Street Parking (1 parking pass per night provided by host) * Garage parking available for small SUVs and compact vehicles only (trucks and other vehicles must use street parking) *Free Wi-Fi *Comfortable Queen Bd *50' smart TV with all streaming services for you to sign in and enjoy your favorites *Fully Stocked Kitchen + Microwave + Fridge + Coffee/Tea maker The space 5-10min walk > lots of restaurants/Local Gambling Slots 10min drive > Mall/Oak Park/Hospitals/Brookfield Zoo 20min drive> Medical District/Medicine/Doctors 25min drive> Ohare & Midway airport/Northwestern/Rivers-Bally Casino/Downtown Chicago/Golfing

Indoor spacesFamilyAir conditioning

4.85 out of 5 average rating, 151 reviews

The kitchenette area includes a stainless steel refrigerator, a microwave, and a Kuerig coffee maker on a pull-out countertop. Below are white cabinets providing storage space, with the upper wall featuring light switches and an electrical outlet.

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"

KitchenIndoor spacesTV

4.85 out of 5 average rating, 170 reviews

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

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

KitchenFamilyView

4.94 out of 5 average rating, 886 reviews

A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.

Treehouse in Schaumburg

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot/cool tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Indoor spacesFamilyWifi

4.97 out of 5 average rating, 133 reviews

A bright living area with a sloped ceiling features a comfortable blue sofa and light-colored armchairs. A small marble-top table is set with two cups. A desk is positioned near a window, and a decorative rug adds warmth to the hardwood floor.

Guesthouse in Oak Park

Oak Park cozy carriage house-lovely, walkable area

Our comfortable, stylish retreat has everything you need to relax and recharge. Whether you are visiting to explore all that beautiful Oak Park and downtown Chicago offer or desire a peaceful space to work. -> Quiet, walkable street near popular cafes, restaurants, taverns, parks, historic homes -> Steps from the "L" Blue Line Oak Park station -> Stocked w/ snacks + gourmet coffee/tea set-up (grinder, AeroPress, and Keurig) -> Onsite off-street parking -> A/C + heat -> garden sitting area

FamilyKitchenHospitality

4.91 out of 5 average rating, 537 reviews

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

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 twin sofa bed, + 2 twins available on request. 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! (Yes, I truly needed to add the “no glitter” rule! (You can only imagine!)

Indoor spacesKitchenSolo travel

4.97 out of 5 average rating, 230 reviews

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

Home in Berwyn

RetroModern Bungalow | free parking | pet friendly

Experience the city in style at our 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 pup-friendly, fenced-in backyard. With central HVAC, speedy WiFi, a dedicated workspace, and a pack-n-play crib 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 and catch the train a few blocks away.

Indoor spacesFamilyLong stay

4.88 out of 5 average rating, 103 reviews

A cozy living room features four plush purple chairs arranged around a circular table. A modern television is mounted above a white brick fireplace, complemented by bookshelves filled with various items. A large potted plant adds a touch of greenery, enhancing the warm atmosphere.

Home in Oak Park

A Comfortable Stay While You are Away in Oak Park

Welcome to this Oak Park home, conveniently minutes from the main expressway, train station, downtown Chicago, and the Medical Center. This entire Oak Park house is ideal for travelers seeking a tranquil and welcoming space to unwind in after a long day, medical professionals, visiting patients at the Medical Center, and families needing long-term housing. The residence is minutes from downtown Oak Park and the historical landmarks of Frank Lloyd Wright's home and studio.

KitchenFamilyPets

4.83 out of 5 average rating, 115 reviews

A well-lit sleeping area features a spacious bed adorned with patterned linens and accent pillows. A wooden nightstand holds a lamp. A clothes rack stands nearby, alongside a chair with a throw pillow. Dark curtains frame a window, adding privacy to the room.

Apartment in Oak Park

Bright Boho Haven free parking

Welcome to our bright, newly constructed 1-bedroom, 1-bath Airbnb in the heart of Oak Park. Enjoy a sunny, modern space with a beautiful bathroom, free parking, and all the essentials. Just steps from grocery stores, coffee shops, and the Oak Park Blue Line stop—reach downtown Chicago in under 30 minutes. Perfect for a cozy getaway or work trip, with fast Wi-Fi, smart TV, kitchenette (no oven!) and a peaceful, walkable neighborhood. We can’t wait to host you!

Indoor spacesKitchenWifi

4.99 out of 5 average rating, 104 reviews

A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.

Home in Brookfield

Cozy Home in Brookfield

Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).

FamilyKitchenParks

4.99 out of 5 average rating, 153 reviews

A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.

Home in Lombard

Modern Boho house in Lombard 7 min to Metra

Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!

KitchenFamilyCondition

4.98 out of 5 average rating, 269 reviews

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

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.

KitchenIndoor spacesSleep quality

Popular amenities for Berwyn family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.88 out of 5 average rating, 101 reviews

A spacious living room features a rich blue accent wall and mid-century modern furniture. Two armchairs and a plush sofa are arranged around a low coffee table. A television is mounted on the wall, complemented by decorative wall art. Natural light fills the room.

Home in Westchester

Modern 2Bdrm Westchester/Chicago Home.With Hot tub

KitchenFamilyGrill

4.93 out of 5 average rating, 280 reviews

A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.

Condo in Little Italy

Private hot tub - King bed suite - Free parking

FamilyKitchenSleep quality

4.92 out of 5 average rating, 128 reviews

Home in Carol Stream

Lake Home Retreat-HotTub• FirePit• Kayak• Fishing!

Indoor spacesKitchenSleep quality

4.88 out of 5 average rating, 390 reviews

The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.

Guesthouse in Chicago

Private Coach house near Lincoln Square!

Indoor spacesKitchenLocation

4.97 out of 5 average rating, 180 reviews

Condo in West Town

Chicago Oasis | Spa Bath, Patio & Fireplace

Indoor spacesFamilyOutdoor spaces

Condo in Ukrainian Village

The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.

4.98 out of 5 average rating, 121 reviews

Ukrainian Village 3BR/3BA • Private Patio, Parking

Indoor spacesKitchenSleep quality

4.96 out of 5 average rating, 178 reviews

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Bridgeport

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

KitchenFamilyBackyard

4.86 out of 5 average rating, 108 reviews

A spacious living room features comfortable seating on soft gray furniture, including a large chaise and armchairs. Natural light brightens the area, while a gas fireplace is set within a stylish stone surround. A large flat-screen TV is mounted above the fireplace.

Home in Lake View

Entire house in Lakeview with yard and garage

KitchenFamilyAir conditioning

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 221 reviews

A cozy living room features a dark sectional sofa adorned with yellow accent pillows, set against a reclaimed wood wall. Large windows allow natural light to fill the space, complementing a neutral area rug that anchors the seating arrangement.

Home in Oak Park

Cozy & comfy w/free parking & W/D

KitchenFamilyCheck-in

5.0 out of 5 average rating, 385 reviews

A spacious bedroom features a large bed with dark bedding and decorative pillows. A wooden bookshelf filled with books stands against one wall, while sunlight filters through a window adorned with light curtains. A vintage dresser and bedside table complete the welcoming space.

Apartment in Forest Park

Like a Treehouse!

KitchenFamilyHospitality

4.88 out of 5 average rating, 181 reviews

A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.

Loft in Brookfield

1920s fully updated unique open artist loft space

KitchenFamilyLaundry

4.87 out of 5 average rating, 417 reviews

A two-story apartment building is shown, featuring a light-colored exterior with dual-tone siding. Lush greenery surrounds the structure, including shrubs and grass. A staircase leads to the entrance, while the nearby homes display varying architectural styles.

Apartment in Forest Park

Home in Forest Park downstairs.

FamilyIndoor spacesBackyard

4.8 out of 5 average rating, 213 reviews

A spacious living area showcases a light brown sectional sofa positioned around a coffee table. Two large televisions are visible in the background, framed by dark curtains. A decorative rug and plants add warmth to the room, which is illuminated by natural light.

Guest suite in Oak Park

Private 2 BR Oak Park Garden Apt

Indoor spacesKitchenHospitality

Apartment in Little Italy

A bright and open living space showcases a contemporary seating area with a green sofa and a plush armchair. Natural light floods through large windows, casting a warm glow over the stylish kitchenette and dining table. A smart TV is mounted on the wall, enhancing the modern vibe.

4.9 out of 5 average rating, 170 reviews

Modern 1BR in Little Italy, Near West Loop

Indoor spacesKitchenLayout

4.87 out of 5 average rating, 151 reviews

Apartment in Oak Park

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

KitchenIndoor spacesBathroom

4.89 out of 5 average rating, 344 reviews

A comfortable sleeping area features a spacious bed adorned with a decorative pillow displaying a tree branch design in earthy tones. Soft lighting from two bedside lamps provides a warm glow, while a piece of framed art hangs above the bed against a muted green wall.

Home in Forest Park

Charming dog friendly 2-Bath Bungalow Near Chicago

KitchenIndoor spacesParking

Family-friendly home rentals with a pool

Condo in Elk Grove Village

The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.

4.92 out of 5 average rating, 122 reviews

Just remodeled apartment close to airport and mall

KitchenFamilyHospitality

4.96 out of 5 average rating, 121 reviews

The living area features a comfortable sofa adorned with patterned cushions, accompanied by a stylish coffee table. A modern dining setup is visible in the background, along with sleek kitchen cabinetry. Light from overhead fixtures illuminates the open layout with dark hardwood flooring.

Condo in Evanston

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

FamilyKitchenQuiet

Apartment in Logan Square

An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.

4.98 out of 5 average rating, 168 reviews

Fun & cozy getaway w/POOL/game room/FREE parking

Indoor spacesKitchenOutdoor spaces

4.9 out of 5 average rating, 599 reviews

A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.

Apartment in Uptown

Whole Flat in Private Club. Walk to L, Dining & Shows

Indoor spacesFamilyHeating

Apartment in Chicago Loop

A bright living area features large windows that offer city views, enhanced by natural light. Comfortable gray seating is arranged on a patterned rug, complemented by modern decor and greenery. A flat-screen TV is mounted on the wall, alongside a stylish coffee table.

4.81 out of 5 average rating, 351 reviews

Spectacular 2BR Penthouse in the Loop | Roof Deck

Indoor spacesKitchenView

Apartment in Downtown Chicago

A large outdoor pool is surrounded by a modern deck featuring lounge chairs. High-rise buildings provide a city backdrop against a clear blue sky.

4.92 out of 5 average rating, 117 reviews

Highrise Hideout (Fitness Center • Sauna)

Indoor spacesFamilyTV

Apartment in Downtown Chicago

4.93 out of 5 average rating, 123 reviews

Gold Coast Luxury: 2BR with Sweeping City Vistas

Indoor spacesKitchenWalkability