House vacation rentals in Berwyn

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.

LocationValueSleep quality

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

FamilyValueWalkability

4.97 out of 5 average rating, 232 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.

LocationValueParking

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!

ValueLocationCondition

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

Welcome to BoHo House – a charming, airy bohemian gem built in 1903. This beautifully designed 3BR home is just a short walk from Chicago's popular bars, restaurants, and coffee shops. Enjoy the peaceful private fenced backyard, perfect for your pup to roam, complete with an adorable outdoor space. Host a cozy patio dinner by the fire or unwind indoors with a movie. Just 20 minutes from ORD, 10 minutes to downtown, with 800+ Mbps WiFi, free coffee, and secure 2-car garage parking!

FamilyLocationLayout

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.

ValueLocationBackyard

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.

FamilyLocationAmenities

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).

ValueLocationComfort

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.

4.97 out of 5 average rating, 143 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.

ValueFamilyNearby

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!

ValueLocationLaundry

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!

FamilyLocationCheck-in

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

Enjoy a stylish experience at this centrally located home in Westchester, IL. Our home is just 20mins away from downtown Chicago, approx. 10mins away from Premium Oak Brook mall and just 20mins away from Rosemont shopping center. Public Transportation is within walking distance from the home. This beautiful home sits in a peaceful neighborhood for a perfect relaxation getaway.

LocationValueQuiet

Popular amenities for Berwyn house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 60 reviews

Home in Schaumburg

Backyard Paradise/ Private Pool + Peaceful Stay

FamilyValueCleanliness

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

LocationFamilyQuiet

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

FamilyLocationCheckout

Superhost

A sparkling pool is framed by a spacious patio, featuring lounge chairs and tables for relaxation. Nearby, a playground is visible, along with a covered seating area and a Blackstone grill, all surrounded by greenery and a serene setting.

Home in Plainfield

4.8 out of 5 average rating, 60 reviews

Pool, 30 mins to CHI, 3 Kings, Outdoor Space, BBQ

ValueLocationComfort

4.87 out of 5 average rating, 30 reviews

Home in Bridgeport

PRIME 2BD Designer Retreat & Pool |Parking| Patio

FamilyLocationGetting around

4.83 out of 5 average rating, 6 reviews

Home in Skokie

Luxury fenced in modern ranch

FamilySleep qualityAmenities

Superhost

Home in West Loop

4.72 out of 5 average rating, 60 reviews

Chic Fulton Market Oasis + Curated Comfort & Style

ValueLocationSleep quality

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+

FamilyLocationBathroom

Weekly house rentals

4.86 out of 5 average rating, 181 reviews

The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.

Home in Naperville

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

ValueFamilyAir conditioning

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!

ValueFamilyQuiet

4.88 out of 5 average rating, 144 reviews

A comfortable living area features a blue couch adorned with decorative pillows, complemented by a lighted lamp on a small side table. Two chairs are positioned nearby, and a patterned area rug covers the hardwood floor, while natural light filters through the windows.

Home in Forest Park

Adorable house Madison Street w/ 2 car garage!

LocationFamilyPets

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

LocationFamilyNearby

4.96 out of 5 average rating, 300 reviews

A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.

Home in Wicker Park

Division St Designer Home In Heart of Wicker Park

LocationValueSleep quality

4.98 out of 5 average rating, 211 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

FamilyLocationSolo travel

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

ValueLocationAmenities

4.94 out of 5 average rating, 120 reviews

A ranch-style home is showcased with a welcoming facade of brick and siding. Large windows provide ample natural light, while a well-maintained garden features a variety of colorful flowers. A manicured lawn and sidewalk lead to the entryway, enhancing the inviting exterior.

Home in Worth

Worth It! 3 bedroom ranch home

ValueFamilyBackyard

Private house rentals

5.0 out of 5 average rating, 60 reviews

Home in Forest Park

2 BR • CTA Blue Line to Chicago • Free Parking

ValueLocationCheck-in

4.95 out of 5 average rating, 19 reviews

Home in Brookfield

Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard

FamilyLocationShared spaces

5.0 out of 5 average rating, 34 reviews

Coach House•Theater•Parking•6 minute Walk to FLW

LocationFamilyNearby

4.9 out of 5 average rating, 61 reviews

A modern kitchen is showcased with dark cabinetry and a contrasting light countertop. Stainless steel appliances, including a refrigerator, microwave, and oven, are featured. A patterned tile border adds visual interest to the space, while large windows provide natural light.

Home in Brookfield

Beautiful home near the Windy City!

FamilyValueAccuracy

4.97 out of 5 average rating, 65 reviews

Home in Berwyn

5 Star Upscale Entire Family Neighborhood Home

ValueLocationLayout

A remodeled kitchen features a large island with three wooden stools and a copper accent. A vintage red refrigerator stands against a backdrop of grey cabinets and an exposed wooden beam ceiling. Open shelves showcase kitchenware alongside rustic decor elements.

4.99 out of 5 average rating, 77 reviews

Oak Park - Wine House!

ValueLocationGetting around

4.9 out of 5 average rating, 30 reviews

Home in South Side

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

FamilyLocationIndoor spaces

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.