Family-friendly holiday rentals in Berwyn

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.

4.83 out of 5 average rating, 117 reviews

House to Relax

Elegant/Spacious 2bd Apt close to Chicago Stay includes: * 1 FREE parking spot in garage for most vehicles including regular size trucks. (Clearance 7’) *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

FamilyIndoor spacesAir conditioning

4.86 out of 5 average rating, 157 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"

Indoor spacesKitchenLocation

5.0 out of 5 average rating, 103 reviews

Oak Park Space+Style Duplex Parking+Walk to Train

A warm, curated home with two floors of living space. Perfect for families with kids, groups of friends and multi-generational living. The main floor + finished basement total 3 bdrms + 2.5 baths. Primary suite is on the main floor. Two secondary bedrooms are on the lower w/ a full bath. 20 min to downtown Chicago. Walk to dining + train+ FLW Home. Open living/dining/kitchen/sunroom. Remote work space. Coffee bar. Private entry/deck. Driveway parking. Central AC. Upstairs apartment is separate.

FamilyKitchenBathroom

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.

4.85 out of 5 average rating, 176 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 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

FamilyIndoor spacesAir conditioning

4.91 out of 5 average rating, 269 reviews

A spacious bedroom is furnished with a large bed featuring a gray and white patterned blanket. Art pieces are displayed on the wall above the bed, and two bedside lamps with warm light sit on either side. A bold, geometric area rug adds texture to the space.

Guest house in Oak Park

Gallery Loft of Oak Park #1 Top Host in IL

Gallery Loft of Oak Park <a href="https://news.airbnb.com/the-number-one-new-host-in-each-us-state/">2021 #1 Top Host in Illinois</a> is a Chicagoland gem near the birthplace of Ernest Hemingway, Frank Lloyd Wright Home/Studio. 2nd story flat furnished in vintage mcm style, featuring local artists. Walking distance to live music (Fitzgerald's, Friendly Music Community), and restaurants. Firepit access, easy street parking and kitchen well stocked. Private porch. Perfect long/short term stays.

FamilyIndoor spacesTV

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.

4.91 out of 5 average rating, 553 reviews

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!)

KitchenIndoor spacesDecor

4.98 out of 5 average rating, 245 reviews

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

retro modern bungalow | a pet friendly pad

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.

FamilyIndoor spacesWalkability

4.98 out of 5 average rating, 162 reviews

The Chicago Game Room (Oak Park, IL)

There is no other rental like this in the Chicago area! Located in the first suburb west of Chicago, this 4-bedroom, two-level private apartment is brand new and ready for your group to enjoy. It features an amazing game room/living room with cathedral ceilings, skylights, gas fireplace, bar seating, pool table, shuffleboard/bowling table, dart board, four bedrooms + sleeper sofa, full kitchen, spa-like bathrooms, in-unit washer/dryer, and private deck. GUESTS = 8 MAX

Indoor spacesFamilyLocation

4.91 out of 5 average rating, 162 reviews

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

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.

KitchenFamilyGetting around

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.

4.84 out of 5 average rating, 126 reviews

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!

KitchenIndoor spacesDecor

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.

4.95 out of 5 average rating, 346 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.

Indoor spacesKitchenValue

4.87 out of 5 average rating, 198 reviews

A bright living room is featured, displaying a blue sofa and yellow chairs arranged around a coffee table. A large clock adorns the blue accent wall, while natural light enters through the window. A plant adds a touch of greenery, completing the inviting space.

Apartment 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.

Indoor spacesFamilyCheck-in

Popular amenities for Berwyn family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.87 out of 5 average rating, 103 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

FamilyKitchenAir conditioning

4.92 out of 5 average rating, 128 reviews

An outdoor patio is illuminated by string lights, creating a cozy ambiance. The hot tub is set against a backdrop of snowy ground, with comfortable seating arrangements nearby. The lake is visible in the background, enhancing the tranquil atmosphere.

Home in Carol Stream

Lake House Escape •Hot Tub, Bar, Fishing, Firepit

KitchenIndoor spacesSleep quality

4.94 out of 5 average rating, 897 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*)

KitchenIndoor spacesHot tub

Apartment 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.

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

FamilyIndoor spacesLaundry

4.98 out of 5 average rating, 128 reviews

Apartment in Little Italy

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.

Private hot tub - King bed suite - Free parking

FamilyKitchenDecor

4.92 out of 5 average rating, 283 reviews

4.88 out of 5 average rating, 396 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.

Guest house in Chicago

Private Coach house near Lincoln Square!

FamilyIndoor spacesParks

4.96 out of 5 average rating, 187 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

Indoor spacesFamilyParks

Apartment in Logan Square

An elegantly furnished dining area features a wooden table with a textured runner. Dark leather chairs surround the table, and a modern chandelier hangs above. The open kitchen, equipped with stainless steel appliances and bar seating, is visible in the background.

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

KitchenIndoor spacesDecor

4.98 out of 5 average rating, 327 reviews

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 108 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

Indoor spacesKitchenLong stay

4.87 out of 5 average rating, 154 reviews

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

Indoor spacesKitchenLaundry

5.0 out of 5 average rating, 393 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.

Flat in Forest Park

Like a Treehouse!

Indoor spacesFamilyLong stay

4.83 out of 5 average rating, 178 reviews

A spacious living area features a dark sectional sofa adorned with yellow accent pillows, complemented by a cozy throw blanket. A circular mirror hangs above a standing lamp, while decorative wall art adds visual interest. A dining table with chairs is situated in the background.

Home in Oak Park

Urban Chic 3beds w/2bath + free parking & W/D

FamilyKitchenLayout

4.98 out of 5 average rating, 422 reviews

The living area features a comfortable sofa, paired with two woven armchairs. A rustic wooden coffee table sits at the center, adorned with a vase of fresh flowers. Natural light illuminates the space through two large windows, framed by soft curtains.

Flat in Forest Park

Walk to Oak Park from Our Sunny Turn of the Century Apt

Indoor spacesFamilyCleanliness

4.88 out of 5 average rating, 106 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

KitchenFamilyAir conditioning

4.97 out of 5 average rating, 186 reviews

A spacious living area showcases a comfortable gray sectional sofa and a reclining chair. A contemporary coffee table rests on an area rug with floral patterns. A mounted TV is visible alongside a wooden credenza featuring a coffee maker and supplies, enhancing the functionality of the space.

Home in Forest Park

Gather in Spacious 3 Bedroom 2 Bath Retreat

Indoor spacesFamilyCondition

4.89 out of 5 average rating, 141 reviews

Home in Oak Park

Steps to Shops, Restaurants, Trains; 5BR, 14 Guest

Indoor spacesFamilyParking

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 172 reviews

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.

Flat in Logan Square

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

Indoor spacesKitchenBack garden

Apartment 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.

Just remodeled apartment close to airport and mall

Indoor spacesKitchenCondition

4.92 out of 5 average rating, 127 reviews

4.96 out of 5 average rating, 122 reviews

An open-concept living space is showcased, featuring modern kitchen appliances, a dining table with seating for six, and a comfortable sofa. Large windows allow natural light to fill the area, providing views of the outdoor landscape.

Apartment in Evanston

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Indoor spacesFamilyBathroom

4.93 out of 5 average rating, 124 reviews

A rooftop pool area features a long, inviting pool bordered by lounge chairs in various colors. Sunlit trees are visible nearby, and the backdrop consists of modern high-rise buildings, creating a vibrant urban atmosphere.

Flat in Downtown Chicago

The Metropolitan Retreat (Fitness Center • Sauna)

Indoor spacesFamilyCheck-in

4.81 out of 5 average rating, 359 reviews

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.

Flat in The Loop

Spectacular 2BR Penthouse in the Loop | Roof Deck

FamilyKitchenPets

4.93 out of 5 average rating, 131 reviews

The modern kitchen features white cabinetry and a spacious island with four bar stools. A stainless steel refrigerator stands next to a gas stove and microwave. Natural light filters through large windows, illuminating the elegant countertops and sleek finishes.

Flat in West Town

Cozy Duplex Down in Wicker Park East w/ Parking

Indoor spacesFamilyTV

4.9 out of 5 average rating, 600 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.

Flat in Uptown

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

KitchenIndoor spacesGrill