House holiday rentals in Skokie

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.

4.95 out of 5 average rating, 121 reviews

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.

ValueFamilyGetting around

4.98 out of 5 average rating, 212 reviews

The living area features a cozy sofa and a patterned armchair, complemented by a glass coffee table. A television is positioned in one corner. Large windows invite natural light, while floor-to-ceiling curtains offer privacy. A potted plant adds a touch of greenery.

Home in Wilmette

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

ValueFamilyNearby

4.98 out of 5 average rating, 131 reviews

Home in Northbrook

*King bed *Outdoor Living *Sought-After Area

Welcome to our sophisticated ranch style home, nestled in the serene, central Chicago neighborhood of Northbrook. This carefully curated home offers a peaceful retreat in a walkable neighborhood with nearby shopping and dining. With its elegant decor, comfortable furnishings, and modern amenities, the home provides a haven of relaxation. Whether you're enjoying a cup of coffee on the private patio or exploring the area, this home provides the perfect backdrop for a memorable vacation experience.

LocationValueSleep quality

A spacious kitchen area is shown with modern stainless steel appliances and ample cabinet storage. A large wooden dining table is centered, set with decorative placemats. Soft light illuminates the room, complementing the neutral color scheme of the walls and cabinetry.

4.97 out of 5 average rating, 119 reviews

Newly remodeled O’hare oasis

Your family will be close to everything when you stay at this centrally-located place. This 3 bed 2 bath newly remodeled private home will have everything you need to feel comfortable during your stay! You are 3 miles from O’Hare airport ,2 miles from Rivers Casino, 1 mile from Allstate Arena, and 4 miles from Fashion outlet mall of Chicago. Enjoy spacious living room and Rec Room, large eat-in kitchen with all new appliances! King bed . 2 queen Beds and pullout sofa with queen bed for sleeping

FamilyValueHeating

4.96 out of 5 average rating, 208 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

LocationValueDecor

A stylish living area features a comfortable blue couch adorned with decorative pillows. A glass coffee table sits atop an area rug, surrounded by an array of colorful artwork on the walls. A cozy sleeping area is visible in the background, draped with vibrant blankets.

4.86 out of 5 average rating, 251 reviews

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

ValueLocationParks

4.99 out of 5 average rating, 151 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!

First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!

LocationFamilyKitchen

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, 136 reviews

Victorian House in Heart of Rogers Park

Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

LocationValueSleep quality

The exterior of a two-story home is depicted, featuring a combination of white and black siding. A prominent bay window enhances the facade, while landscaped flower beds with red mulch and small plants frame the entrance. Green grass and a sidewalk lead up to the house.

4.9 out of 5 average rating, 178 reviews

Cozy Home by O'Hare + EV Plug

Family-friendly 3BR/2BA home in Des Plaines! Enjoy arcade games, board games, and an EV charger. Nestled in a quiet neighborhood near parks, shopping, and entertainment. Just minutes from Des Plaines Theatre, Rivers Casino, Mystic Waters, and Fashion Outlets of Chicago. Ideal for families or groups seeking comfort, fun, and convenience with easy access to top attractions and O'Hare Airport. Your perfect home base for exploring the Chicago area!

LocationValueWalkability

4.99 out of 5 average rating, 105 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).

FamilyValueDecor

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, 103 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.

FamilyLocationPets

4.97 out of 5 average rating, 143 reviews

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.

Home in Oak Park

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.

LocationValueSleep quality

Popular amenities for Skokie house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.83 out of 5 average rating, 6 reviews

Luxury fenced in modern ranch

FamilyConditionSleep quality

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.

4.93 out of 5 average rating, 27 reviews

Paradise with Pool & Games

FamilyLocationKitchen

4.97 out of 5 average rating, 60 reviews

Backyard Paradise/ Private Pool + Peaceful Stay

FamilyValueComfort

Superhost

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

5.0 out of 5 average rating, 3 reviews

Riverwoods Nature Retreat

FamilyLocationAccuracy

4.87 out of 5 average rating, 31 reviews

Home in Bridgeport

PRIME 2BD Designer Retreat & Pool |Parking| Patio

FamilyLocationCheck-in

Superhost

Home in West Loop

4.72 out of 5 average rating, 60 reviews

Chic Fulton Market Oasis + Curated Comfort & Style

ValueFamilyIndoor spaces

4.89 out of 5 average rating, 18 reviews

The exterior of a spacious two-story home is shown, featuring a mixture of brick and siding. Lush green landscaping surrounds the house, with trees casting shade across the front yard. A paved driveway leads to a garage, and a clear blue sky provides a bright backdrop.

Home in Carol Stream

Spacious 4 Bed/3.5 Bath Sleeps 8+

LocationFamilyGetting around

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

LocationFamilyKitchen

Weekly house rentals

4.94 out of 5 average rating, 183 reviews

A cozy living room features a pair of light-colored sofas and an accent chair, positioned around a rustic coffee table. A patterned area rug lies underfoot, while a mirror with a wooden frame and wall art enhance the space. A partial view of the kitchenette is visible in the background.

Home in Highland Park

Cozy 2-Bedroom Cottage Near Downtown Highland Park

LocationFamilyCheck-in

The exterior of a modern ranch-style home is showcased, featuring a strategic arrangement of greenery and colorful landscaping. A paved driveway leads to a welcoming entrance, flanked by two garage doors. The home is complemented by a clear blue sky and mature trees in the background.

4.93 out of 5 average rating, 98 reviews

Cozy Schaumburg 5 br/3.5ba w/ bonus rooms/office

LocationValueAccuracy

The spacious family room features a high vaulted ceiling with exposed wooden beams. A stone fireplace provides a central focal point, and a large TV is mounted above it. Comfortable seating is arranged for relaxation, complemented by a stylish area rug.

4.97 out of 5 average rating, 131 reviews

NEW~2 Spa Baths~Game Room~Prime Area~Big Yard~

FamilyValueCheckout

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

LocationValueOutdoor spaces

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.

4.95 out of 5 average rating, 119 reviews

Pet-Friendly Sunny 3BR Near Woodfield & Downtown

LocationFamilyBackyard

4.99 out of 5 average rating, 165 reviews

Home in Wrigleyville

Whole apartment! 2 Bed/2 bath steps from Wrigley!!

LocationFamilyBathroom

A bright living area features a modern design with large windows allowing natural light. Two armchairs are positioned near a white coffee table, complemented by a leather sofa draped with a soft throw. Light-colored curtains frame the windows, creating a soft ambiance.

4.93 out of 5 average rating, 88 reviews

Luxury Home - Pool Tbl/Bar/Patio

LocationFamilyAccess

The open living area features a spacious sectional sofa facing a modern stone fireplace. A wall-mounted smart TV is visible above the fireplace, while a kitchen island with bar seating is positioned nearby. Natural light enters through windows, enhancing the neutral decor.

5.0 out of 5 average rating, 49 reviews

Casa 22 Luxury & Modern 3BD 2BA Home in Skokie

LocationFamilyLayout

Private house rentals

4.75 out of 5 average rating, 24 reviews

Modern Cozy Retreat by O’Hare

LocationValueBeach

A bright bedroom features a metal bed frame with a spacious white bedding set. Two nightstands with lamps are positioned on either side. Natural light filters through the large window, highlighting the room's neutral walls and wooden flooring.

4.99 out of 5 average rating, 69 reviews

Amazing Location! Spacious Duplex Getaway

LocationFamilyGetting around

Superhost

4.67 out of 5 average rating, 6 reviews

Parisian Inspired Escape | Close to Town & NU

ValueLocationKitchen

4.92 out of 5 average rating, 64 reviews

The living area features two comfortable gray sofas facing a low coffee table, with a wall-mounted TV displaying a nature scene. Large windows allow natural light to fill the space, and a potted plant adds a touch of greenery. Soft area rug enhances the inviting atmosphere.

Home in Wilmette

Luxury Home- NorthShore/Wilmette

FamilyValueKitchen

The living area features a light gray sectional sofa, paired with two accent chairs in shades of green. A round coffee table is centered on a textured area rug, with a modern floor lamp providing ambient light. A console table and artwork adorn the walls.

4.86 out of 5 average rating, 29 reviews

Renovated Mid-Century, 4 bed/2.1 bath townhome

ValueLocationAccuracy

A spacious living area features plush blue sofas and a round marble coffee table. A large television is positioned on a wooden stand, while a modern kitchen with a breakfast bar is visible in the background. Natural light illuminates the space, enhancing its inviting atmosphere.

4.81 out of 5 average rating, 43 reviews

Stokes Stay: Stunning 4BR/2.5BT

LocationFamilyBathroom

4.98 out of 5 average rating, 47 reviews

Large and Lovely Home w 4 Floors of Living

LocationFamilyQuiet

The spacious kitchen includes high-end Viking stainless steel appliances, granite countertops, and ample wooden cabinetry. A large center island with barstool seating invites casual dining. Natural light fills the room through a skylight, enhancing the warm wood tones of the cabinetry and flooring.