House holiday rentals in Oak Park

4.95 out of 5 average rating, 120 reviews

A single-story brick house is presented with a spacious front yard, featuring trimmed greenery and a walkway of stone steps leading to the front door. A driveway, visible to the right, accommodates a garage door with a dark finish.

Home in Skokie

Cozy 2 bedroom house/w garage in Skokie

Charming 2B/1.5B house in Skokie IL. This Airbnb boasts plenty of amenities including WIFI, Roku TV's, fully furnished, a beautiful backyard, workout gym and sauna in the basement and a kitchen with top of the line appliances. The house sits on a quiet residential street just 2 minutes away from the nearest interstate taking you to beautiful Downtown Chicago in about 25min . Downtown Skokie is a few minutes away, plenty of shopping options 5min to Village Crossing and 15min to Old Orchard Mall.

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A cozy living room features a gray sofa with decorative pillows, a round dining table with chairs, and a stone fireplace. Natural light enters through windows adorned with decorative molding, while a few bookshelves provide a space for books and decor. A colorful area rug adds warmth to the hardwood floor.

4.96 out of 5 average rating, 236 reviews

Cozy, Walkable Apt. w/ Kitch. & Parking for 4

Enjoy our historic district three-flat w/ free parking in upscale, safe Oak Park just 3 blocks to the train, easy access to Chicago. Enjoy some tranquil time in our little eco suburban farm. Check out the gardens and visit our 6 friendly chickens. This non-smoking apartment w/ full kitchen is perfect for tourists, couples, or business travelers. We require no check-out chores. Easy highway and airport access. No parties. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

FamilyValueHospitality

4.96 out of 5 average rating, 207 reviews

A private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.

Home in Chicago

The Chicago River House – GIANT wall projector!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

LocationFamilyBiking

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.

4.97 out of 5 average rating, 231 reviews

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.

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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

Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

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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.

4.88 out of 5 average rating, 103 reviews

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.

LocationFamilyAccuracy

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).

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Home in Elk Grove Village

A bright living area is presented with a light-colored sofa and a welcoming cushion. Colorful floral artwork decorates the wall above. A round, dark wood coffee table is centered, complemented by a small planter with decorative flowers and a potted plant in the corner.

4.93 out of 5 average rating, 102 reviews

Modern Aesthetic 3bd Family Haven w/ King Bd, Yard

Unwind in this spacious, family-friendly haven in Elk Grove Village. Featuring a king bed, modern amenities, and a private yard, it’s the perfect spot for a relaxing getaway or a convenient home base to explore the area. The home is centrally located near O'hare Airport and Woodfield Mall, plus it is conveniently located near the intersection of Chicago's two major highways: I-90 and I-290, ready to take you to your destination.

FamilyLocationIndoor spaces

A charming Victorian home is showcased, featuring a front porch with wide steps leading to a door framed by lush greenery. The exterior is painted in a crisp white, complemented by dark accents on the windows. A manicured lawn adds to the inviting landscape.

4.96 out of 5 average rating, 142 reviews

Oak Park Victorian by FLW Studio

Discover historic charm in our updated 4-bedroom Victorian home in the iconic Frank Lloyd Wright district. Comfortably sleeps 8. Features a fully equipped kitchen, dedicated workspace, and modern amenities. Perfectly located for exploring local gems on foot or a quick 15-min drive to downtown Chicago. Enjoy private parking and easy access to public transit. Ideal for families and groups seeking a stylish, central retreat.

LocationValueCheckout

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!

LocationFamilyComfort

4.89 out of 5 average rating, 140 reviews

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

Experience a spacious, pet-friendly 5-bedroom, 3-bath home in vibrant downtown Forest Park, perfect for family gatherings or group vacations. Comfortably sleeps up to 14 guests. Enjoy stylish interiors, a fully equipped kitchen, private outdoor spaces, and easy walkability to Madison Avenue's dining and shops. Convenient access to Chicago trains and private parking for 4 vehicles make this an ideal retreat.

ValueLocationAccess

4.83 out of 5 average rating, 109 reviews

Home in Des Plains

Cozy Home near O'Hare & fun Hubs

Relax with the whole family at this peaceful place to stay. Experience comfort and convenience at our newly remodeled cozy house, perfectly situated near O'Hare Airport, Allstate Arena, and Rosemont Theater. Ideal for travelers and entertainment enthusiasts, this charming Airbnb offers modern amenities and a warm ambiance, ensuring a delightful stay. Book now and enjoy the best of Rosemont!

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Popular amenities for Oak Park house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.72 out of 5 average rating, 60 reviews

Home in West Loop

Chic Fulton Market Oasis + Curated Comfort & Style

ValueFamilyWi-Fi

4.87 out of 5 average rating, 30 reviews

Home in Bridgeport

PRIME 2BD Designer Retreat & Pool |Parking| Patio

LocationFamilyWalkability

4.93 out of 5 average rating, 27 reviews

A spacious living area features a light-coloured sofa set positioned around a wooden coffee table, with a television mounted on the wall. A large area rug enhances the space, while plants and natural light provide a fresh atmosphere. Dining space is visible in the background.

Home in Schaumburg

Paradise with Pool & Games

LocationFamilyPets

4.83 out of 5 average rating, 6 reviews

Home in Skokie

Luxury fenced in modern ranch

FamilySleep qualityDecor

5.0 out of 5 average rating, 14 reviews

A light-filled living room features a large sectional sofa and multiple accent chairs arranged around a central rug. A cozy fireplace is flanked by built-in shelves displaying decorative items. A vibrant painting and colorful decor enhance the welcoming atmosphere.

Home in Evanston

1/2 mile to NU, 5min walk to Lake, Swim Spa Pool

LocationFamilyAccuracy

5.0 out of 5 average rating, 3 reviews

An outdoor swim spa is prominently featured, surrounded by a wooden deck and situated amidst a natural setting. The backdrop includes a mid-century modern structure with large windows, nestled among trees and greenery.

Home in Riverwoods

Riverwoods Nature Retreat

LocationFamilyHospitality

4.85 out of 5 average rating, 27 reviews

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.

Home in Glendale Heights

Pardizes Suites

FamilyLocationBackyard

5.0 out of 5 average rating, 26 reviews

A sunny backyard features a round in-ground pool surrounded by lush green grass and vibrant flower pots. The house showcases a two-story design with a balcony and large windows, providing views of the serene outdoor space and nearby landscaping.

Home in Des Plains

Rosemont 4BD2BA house with Pool

ValueLocationParking

Weekly house rentals

4.93 out of 5 average rating, 111 reviews

Home in Brookfield

Remodeled | Game room | Fire Pit | 5 Min to Zoo

FamilyLocationHeating

4.91 out of 5 average rating, 211 reviews

A spacious living area features a vibrant orange sofa adorned with green and beige throw blankets. A stylish coffee table holds decorative items, while a large houseplant adds a touch of greenery. Natural light fills the room, highlighting the wooden staircase in the background.

Home in North Side

BoHo House | Chic, 1903 Chicago Workers Cottage

FamilyValueBarbecue

4.99 out of 5 average rating, 150 reviews

A welcoming living area is presented with a mix of plush seating, including a white chair and a vibrant orange sofa. A wooden shelving unit displays decorative items and books. Soft lighting enhances the wooden floor, while light streams through large windows dressed with sheer coverings.

Home in Ravenswood

Entire first floor in Lincoln Square!

ValueFamilyBathroom

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.

4.91 out of 5 average rating, 158 reviews

Beautiful Bungalow, Near Downtown Chicago

FamilyValueOutdoor spaces

4.94 out of 5 average rating, 108 reviews

A modern kitchen featuring stainless steel appliances, including a refrigerator and gas range. A spacious island with white marble countertop is surrounded by light-colored chairs. Above, stylish pendant lights provide ample illumination, while the open layout invites natural light from adjacent glass doors.

Home in West Town

NEW! 3BR/2.5B Duplex in Noble Sq

ValueLocationWalkability

4.97 out of 5 average rating, 236 reviews

A spacious living area features a dark leather sofa and a modern accent chair beside a circular glass coffee table. A patterned area rug in neutral tones lies on the hardwood floor, while a dining area with a round table and chairs is visible in the background.

Home in Portage Park

The Evergreen House

LocationFamilyQuiet

Home in Rogers Park Township

A stately Victorian house is surrounded by a landscaped garden featuring lush greenery and colorful plants. The front porch is framed by pillars and features multiple seating areas. A red front door adds a bold contrast to the dark exterior of the home.

4.99 out of 5 average rating, 135 reviews

Victorian House in Heart of Rogers Park

LocationValuePets

4.95 out of 5 average rating, 119 reviews

A spacious living area features a large L-shaped sofa adorned with decorative cushions. A coffee table sits at the center, complemented by a cozy area rug. A brick fireplace, currently not in use, adds character, while a wall-mounted Smart TV is positioned above the mantel.

Home in Schaumburg

Pet-Friendly Sunny 3BR Near Woodfield & Downtown

FamilyLocationBackyard

Private house rentals

The kitchen features a spacious layout with a farmhouse sink and modern appliances, including a dishwasher and gas stove. Colorful backsplash tiles add a playful touch. Natural light enters through two windows, illuminating the black marble-like flooring and nearby shelves filled with utensils.

4.87 out of 5 average rating, 63 reviews

Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

FamilyValueKitchen

5.0 out of 5 average rating, 60 reviews

Home in Forest Park

2 BR • CTA Blue Line to Chicago • Free Parking

FamilyLocationParking

5.0 out of 5 average rating, 31 reviews

Oak Park Charm: Arcade Fun, 15 Min to Downtown Chi

FamilyLocationHospitality

4.83 out of 5 average rating, 29 reviews

OakPark Gem. Family-Friendly Getaway near Downtown

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The exterior of the home is showcased, featuring a light-colored facade complemented by neatly trimmed shrubs. Stairs lead up to a welcoming entrance, while a well-kept lawn and mature trees provide shade. The roofline is distinctive, adding character to the overall appearance.

4.92 out of 5 average rating, 71 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

FamilyLocationIndoor spaces

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.

4.97 out of 5 average rating, 38 reviews

The Architectural Haven

LocationValueIndoor spaces

4.83 out of 5 average rating, 53 reviews

Cozy & Peaceful Oasis Near City | 2BR + 1.5 Bath |

FamilyLocationWi-Fi

The exterior of a historic house features a two-story facade with a gabled roof and large windows on the first level. Lush greenery surrounds the property, creating a welcoming atmosphere and enhancing the home’s charm.