Apartment holiday rentals in Naperville

4.91 out of 5 average rating, 287 reviews

An inviting coral front door featuring a bicycle-themed welcome sign. Two bright red mailboxes are mounted beside the door, complementing the cheerful color scheme. Light filters through a sheer curtain in the window above the door, enhancing the welcoming entryway.

Flat in Saint Charles

Vintage Charm

Welcome to The Vintage Charm! This downstairs apartment is 2 beds & 1 bath of Vintage Charm & Cozy Warmth. The walls are plaster, the ceilings are high, the floors are mostly original oak! Please note that new window AC units are in place for cooling & there is a furnace for heat. Entry is via an enclosed front porch. *Cat/Dogs on property, not in Guest Space* *Please submit pictures of any isssues* *Orkin for Pest Control, please contact host with any pest issues to arrange extra service*

4.93 out of 5 average rating, 116 reviews

A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.

Flat in West Dundee

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

A cozy seating area is highlighted by a modern electric fireplace beneath a mounted television displaying streaming options. Soft cushions and a pastel throw blanket add comfort to the light-colored chair. A touch of decor is presented with wall art and a small side table.

4.91 out of 5 average rating, 198 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.

4.87 out of 5 average rating, 700 reviews

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

4.86 out of 5 average rating, 246 reviews

A living area features a dark leather sofa with red accent pillows, paired with two leather chairs. A wooden coffee table sits centrally, surrounded by warm-toned lighting. The space opens to a kitchenette with a retro red refrigerator and tall bar seating, creating an inviting atmosphere.

Flat in Jefferson Park

Cozy & Comfy 1bd In Historic Portage Park Bungalow

Make yourself at home in my comfortable Portage Park one bedroom garden apartment. This spacious condo is bright and airy with warm furnishings, a kitchenette with an island, private bedroom with a full bed and a modern bathroom with a glass walk-in shower. Portage Park is Chicago’s largest Polish neighborhood and is home to vintage charm, heaps of history and classic Chicago-style bungalows. The National Veterans Art Museum is a poignant must-see while you’re here with its combat-era art.

Superhost

A living area is highlighted by a large mural depicting a misty forest. An earthy-toned armchair sits beside a green sectional sofa, while a wooden coffee table holds decorative plants and water bottles. Natural light filters through sheer curtains, enhancing the serene atmosphere.

Flat in Geneva

4.81 out of 5 average rating, 128 reviews

Immaculate*1MiTrain*1GWifi*King*ParkFree*FullKitch

Popular, 2BR/1BA Garden unit. Near downtown Geneva. Hotel Baker 3mi, Equestrian Center 9mi, walk to Fox River Bike Trail, cinemas, bars. Metra Train (1 mi), restaurants, golf, shopping. New cookware, Keurig, kitchen appliances, French press, rice cooker, Insta pot, blender. Bike path 3 blocks. External security cameras at door & public coin laundry area. This unit contains a smoke detector, motion sensor and decibel monitoring device. Guests under 25+ yrs require owner approval.

4.83 out of 5 average rating, 100 reviews

A modern kitchen features dark cabinetry complemented by granite countertops. Stainless steel appliances, including a refrigerator and stove, are present. Two bar stools with circular bases are positioned near the countertop. Pendant lights hang above the island, adding functional illumination to the space.

Flat in Aurora

AT YOUR SERVICE! Downtown Aurora River Facing Gem

Welcome to your cozy retreat in the heart of Downtown Aurora! This charming 1-bedroom apartment is perfect for up to 2 guests and offers a peaceful river view. The unit is complete with a full kitchen & is pet-friendly. Located steps from Hollywood Casino, Paramount Theatre, RiverEdge Park, and the scenic Riverwalk, you'll have easy access to local attractions. Stroll to restaurants, shops, and entertainment, making this the perfect base for exploring all that Downtown Aurora has to offer.

4.99 out of 5 average rating, 200 reviews

A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.

Flat in Aurora

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

4.97 out of 5 average rating, 108 reviews

A comfortable living area is presented with a light-colored sofa draped with a soft blanket. A wooden coffee table sits center stage on a patterned rug. Two decorative lamps illuminate the space, and a bookshelf with various books and a dartboard is positioned against the wall.

Flat in Melrose Park

KNG+QN/1 free parking/18 min to O’hare & Allstate

-18 minutes to O’Hare/Allstate Arena -35 minutes to DT Chicago -King & QN 2 bedroom + sleeper sofa/1 bath apartment decorated with a playful & bright nautical theme & vintage accent pieces. -Board games, books, darts, & large screen TV for entertainment. -Tea & Coffee station -Free designated parking space -walk to local restaurants at corner or playground w/outside seating up the street. -Nothing fancy, but convenient! urban/suburbia vibe in quieter corner of busy central area

4.8 out of 5 average rating, 183 reviews

The exterior of the Victorian Sherwood House showcases its distinct pink siding accented with green trim. Stained glass windows add character, and multiple gabled roofs enhance its architectural design. A canopy of trees provides a natural backdrop to this charming residence.

Flat in Elgin

Sherwood House

Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.

4.94 out of 5 average rating, 144 reviews

A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.

Flat in Lake View

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

Flat in Downtown Naperville

A cozy living area is presented, featuring a comfortable sofa with decorative cushions and a matching ottoman. Two lamps provide soft lighting, and a large mirror reflects the space. A textured area rug defines the seating arrangement, with stair access visible in the background.

4.87 out of 5 average rating, 181 reviews

Comforts of home in downtown Naperville

Cozy 1 bedroom garden level apartment located in downtown Naperville. Short walking distance to great shopping and many fine restaurants. Also short walking distance to train which goes directly to Chicago. Parking is available for 1 car in driveway. Professionally cleaned after every guest visit, as well as free cleaning offered for stays of two weeks or longer.

Popular amenities for Naperville apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

5 out of 5 average rating, 71 reviews

A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.

Flat in Chicago

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

4.87 out of 5 average rating, 15 reviews

A soft blue sofa with white cushions is positioned in the foreground, facing a modern kitchen area. The kitchen features wooden cabinetry, stainless steel appliances, and ample natural light streaming through large windows, illuminating the warm tones of the space.

Flat in Plainfield

Odd Fellows Retreat

5 out of 5 average rating, 63 reviews

A cozy living area is presented with a light-colored sofa adorned with decorative pillows. Two accent chairs in a checkered pattern complement the space, while a wooden coffee table sits at the center. Soft lighting from two bedside lamps enhances the inviting setting, framed by large windows dressed with sheer curtains.

Flat in West Dundee

Charming Downtown Farmhouse Apartment #4

5 out of 5 average rating, 32 reviews

A cozy living room features a comfortable sofa with decorative cushions, set against light-colored walls. A glass coffee table sits in the center, complemented by a small table with an art piece nearby. Natural light flows through a large window, enhancing the inviting space.

Flat in Forest Park

Peaceful One Bedroom Home near Chicago

5 out of 5 average rating, 25 reviews

A cozy living area features a plush gray sofa accompanied by light-colored ottomans. A glass coffee table sits on a multicolored rug, adding warmth to the space. Natural light filters through sheer curtains, enhancing the modern design complemented by a mounted flat-screen television.

Flat in Berwyn

NEW Jade Haven in Berwyn/Riverside

5 out of 5 average rating, 13 reviews

Flat in Warrenville

4BR Townhouse with Lake View & Parking - Sleeps 10

4.99 out of 5 average rating, 97 reviews

A bright living area features a cozy sofa and an armchair, arranged around a small desk workspace. Sliding glass doors open to an outdoor patio area, allowing natural light to fill the room. Soft curtains frame the doors, enhancing the inviting atmosphere.

Flat in Elgin

Peaceful Elgin APT King Bed

4.97 out of 5 average rating, 72 reviews

A modern living space is shown with a relaxation area featuring dark leather seating arranged around a media console. A workspace with a desk and chair is positioned nearby. Soft lighting highlights the dark walls, and art adds a pop of color.

Flat in Hickory Hills

Cozy Guest Suite. Private Entry+ Turo Rental

Private apartment rentals

Double French doors open into a bright, inviting living space. A patterned area rug lays on polished hardwood floors, leading to a cozy seating area with upholstered chairs. Decorative artwork adorns the walls, and soft light filters in through the windows.

4.94 out of 5 average rating, 183 reviews

A Quiet Stay While You Are Away Oak Park

5 out of 5 average rating, 24 reviews

A bright living area features a round glass table surrounded by two yellow chairs with woven backs. A white sideboard and a small microwave are positioned against the wall, complemented by a potted plant. Large windows provide natural light, showcasing the green outdoors.

Flat in Elmhurst

Walk to: Metra to Chicago & Downtown Elmhurst

A spacious living and dining area features a round marble table surrounded by two cozy armchairs. An overhead light fixture illuminates the room, while an archway leads to a dining space with a wooden table and multiple chairs. Warm wooden flooring is present throughout.

4.98 out of 5 average rating, 129 reviews

2-bedroom Apartment in the heart of Oak Park

4.89 out of 5 average rating, 9 reviews

A modern studio space features a spacious seating area with a gray sofa adorned with striped pillows. A sleek coffee table sits in front, while a wall-mounted television is visible. French doors lead to the outside, and soft lighting illuminates the laminate flooring.

Flat in Aurora

Cozy comfortable Studio Condo

4.91 out of 5 average rating, 445 reviews

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.

Flat in Berwyn

Private apartment with retro vibe

5 out of 5 average rating, 42 reviews

A bright bedroom contains a queen bed and a twin bed, both dressed in white linens. Decorative floral art pieces adorn the walls. A bedside table with a lamp is positioned next to the queen bed. Light enters through a window, complemented by light curtains.

Flat in Medinah

Updated 2 Bdrm Oasis - Walk to Train!

A lush garden surrounds a charming historic home, with greenery and flowers creating a vibrant landscape. A shaded seating area is provided under an umbrella, offering a space for relaxation amidst the natural beauty. The home is partially covered in climbing vines, enhancing its character.

5 out of 5 average rating, 84 reviews

Studio Apartment in Oak Park

4.95 out of 5 average rating, 146 reviews

Flat in Irving Park

2BR Near O’Hare • Free Garage Parking • Quiet Stay

Apartment rentals with a hot tub

4.91 out of 5 average rating, 66 reviews

An indoor pool area is featured, highlighting a clean, rectangular swimming pool surrounded by large windows. Lounge chairs are positioned along one side, offering a place to relax. The space is bright with neutral-colored walls and a minimalist design.

Flat in South Loop

The Aerial Oasis

4.97 out of 5 average rating, 33 reviews

A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.

Flat in Fulton Market

Skyline Oasis: City & Lake Views

4.97 out of 5 average rating, 36 reviews

The spacious bedroom features a queen bed and a cozy lounge chair. A light rug covers the hardwood floor, while glass doors open to a private outdoor space. A luxurious jacuzzi tub is visible in the bathroom, along with elegant tile accents.

Flat in Wicker Park

Spacious 1 BR Unit in Wicker Parl|1 FREE G Parking

5 out of 5 average rating, 5 reviews

Flat in West Town

Modern 4BR Retreat in Vibrant West Town

4.97 out of 5 average rating, 144 reviews

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Flat in Dunning

Belmont Pleasures - hot tub / arcade gaming room

4.91 out of 5 average rating, 54 reviews

A private balcony features wooden decking and a wooden railing. Two black wicker chairs with cushions and a matching coffee table create a cozy seating area. Potted plants hang from the railing, and the surrounding neighborhood is visible in the background.

Flat in Albany Park

2Bed 2Bath 15min to Wrigley with Parking& Balcony