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, 111 reviews

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 spacesFamilyAccess

4.85 out of 5 average rating, 150 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 spacesKitchenValue

Superhost

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, 169 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

KitchenFamilyGetting around

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.

4.92 out of 5 average rating, 531 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!)

FamilyIndoor spacesBackyard

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 spacesFamilyAmenities

The exterior of a two-story house is shown, featuring a dark grey facade with white trim. Large windows are adorned with flower boxes displaying colorful blooms. Steps lead to a covered porch, inviting entry into the home.

4.89 out of 5 average rating, 197 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

Indoor spacesFamilyValue

4.88 out of 5 average rating, 102 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.

Indoor spacesFamilyLayout

4.91 out of 5 average rating, 158 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.

KitchenIndoor spacesNearby

Superhost

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.

4.83 out of 5 average rating, 113 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!

FamilyIndoor spacesCondition

4.99 out of 5 average rating, 103 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).

Indoor spacesKitchenBackyard

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.

4.98 out of 5 average rating, 269 reviews

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.

FamilyKitchenHospitality

5.0 out of 5 average rating, 383 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!

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, right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

FamilyIndoor spacesAir conditioning

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

KitchenIndoor spacesGetting around

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*)

Indoor spacesFamilyBathroom

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

KitchenIndoor spacesAmenities

4.92 out of 5 average rating, 128 reviews

Home in Carol Stream

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

FamilyKitchenCheck-in

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!

FamilyIndoor spacesSleep quality

4.97 out of 5 average rating, 180 reviews

Condo in West Town

Chicago Oasis | Spa Bath, Patio & Fireplace

FamilyIndoor spacesLocation

4.95 out of 5 average rating, 177 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 spacesFamilyOutdoor spaces

4.86 out of 5 average rating, 107 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

KitchenFamilyCleanliness

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

KitchenIndoor spacesGetting around

A small, uncomplicated dining area features a black table accompanied by two folding chairs. A decorative yellow vase sits on the table's surface, adding a touch of color. Soft beige walls and a framed picture enhance the space, while a doorway leads to additional rooms.

4.86 out of 5 average rating, 462 reviews

Berwyn Musical Apartment

Indoor spacesFamilyBackyard

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

FamilyKitchenDecor

4.87 out of 5 average rating, 151 reviews

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

Indoor spacesFamilyCheckout

4.81 out of 5 average rating, 212 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

KitchenFamilyAccuracy

4.98 out of 5 average rating, 182 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 spacesFamilyAccess

4.87 out of 5 average rating, 416 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.

KitchenIndoor spacesWi-Fi

4.95 out of 5 average rating, 165 reviews

The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.

Condo in North Side

Lovely top floor 2BR/2BA, steps from everything!

KitchenIndoor spacesCheckout

Family-friendly home rentals with a pool

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, 167 reviews

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

KitchenIndoor spacesAccess

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

Indoor spacesKitchenCondition

4.96 out of 5 average rating, 145 reviews

The living area features a sectional sofa adorned with vibrant cushions beside a coffee table. Natural light filters through large windows dressed with horizontal blinds, illuminating a console with a flat-screen TV and decorative accents.

Condo in Evanston

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Indoor spacesFamilyPool

4.9 out of 5 average rating, 598 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 spacesFamilyHospitality

Apartment in Downtown Chicago

4.93 out of 5 average rating, 122 reviews

Gold Coast Luxury: 2BR with Sweeping City Vistas

FamilyIndoor spacesShared spaces

Apartment in Downtown Chicago

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.

4.93 out of 5 average rating, 119 reviews

The Metropolitan Retreat (Fitness Center • Sauna)

KitchenFamilyAccuracy