Apartment holiday rentals in Gary

4.92 out of 5 average rating, 140 reviews

A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.

Flat in South Side

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

4.97 out of 5 average rating, 119 reviews

A welcoming living area is brightened by natural light streaming through a large window. A comfortable gray daybed is adorned with decorative pillows, complemented by a cozy blue couch. A round coffee table sits on a textured rug, with a potted orchid as a centerpiece.

Flat in Valparaiso

Cozy Casa: Downtown Digs!

Located in the heart of downtown Valparaiso, guests will love this updated, historic charmer! Walk to fabulous restaurants, local shops, or breweries & wineries in minutes. This unit has been fully updated and fully stocked with room to sleep 6. You'll be 25 minutes from the beaches of Lake Michigan/Indiana Dunes National Park, an hour from Chicago, and close to quaint towns and apple/berry picking orchards. This space is perfect for families & friends who want to relax or adventure outdoors!

4.86 out of 5 average rating, 244 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.

An open studio layout features a comfortable seating area with plaid sofas and a wooden coffee table. Light streams through multiple windows, illuminating a spacious sleeping area with a queen size bed. A ceiling fan and wall-mounted TV contribute to a welcoming environment.

4.88 out of 5 average rating, 158 reviews

Heart of Historical Dist.*W/D*Parking*Gl Shower #3

Our charming studio apartment is perfect for a getaway in Northwest IN and will provide everything you need to have an enjoyable stay! Located near Lighthouse Outlets, Restaurants, Casino, Breweries, Indiana Dunes National & State Parks (7 -11.3 miles), Washington Park (1.4 miles) and more! South Shore Line electric train platform is right behind property. (in quiet zone). Day trips are easy to downtown Chicago or South Bend IN. Catch a Notre Dame game one day and see the Bears the next.

A bright living area features a mustard-yellow sofa adorned with decorative pillows. A modern kitchen with stainless steel appliances is visible in the background, while a dining table with four chairs provides a space for meals. Natural light filters in, enhancing the cheerful decor.

4.94 out of 5 average rating, 106 reviews

The Sunshine House: Breezy Beach Unit!

Welcome to Breezy Beach, a bright and cheerful first-floor apartment in the Sunshine House 🌻. With updated amenities, colorful décor, and a prime location near the beach, outlet mall, restaurants, and parks, this spot is perfect for couples, friends, or small families (up to 4 guests). Cook a meal in the fully stocked kitchen 🍳, relax in the comfy queen bed, or enjoy evenings by the outdoor firepit & picnic table. Everything downtown Michigan City has to offer is just a short walk away!

4.85 out of 5 average rating, 311 reviews

A vintage-style sign featuring bold red and white lettering, stating 'Bohemian Lodge no 17' against a dark brown background. Decorative elements include images of beer glasses and whimsical knot designs, creating a nostalgic atmosphere.

Flat in Lower West Side

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

4.87 out of 5 average rating, 101 reviews

A spacious kitchen area is highlighted by a large table with wooden chairs, set against a neutral wall. Natural light filters through the window adorned with wooden blinds. A coffee maker and water bottles are seen on the countertop, with an appliance array visible in the background.

Flat in East Side

Lovely 1-BR Apt with full kitchen & living room

Kick back and relax in this calm, stylish space. We’re super excited to have you as our guest. This apartment is located on the 2nd floor (entrance from outside stairs). We are 30 minutes away from Downtown (no traffic), 4 minutes from Chicago Skyway and 11 minutes from Interstate 94. Enter your space through your own private entrance and make yourself at home. Your unit includes a private 1 Bedroom, 1 Bathroom, a Kitchen, Living Area with a sleeper sofa and desk.

4.93 out of 5 average rating, 122 reviews

The exterior of a two-story duplex is shown, featuring large windows and a welcoming porch. Well-maintained shrubs line the walkway, leading to the entrance. A grassy yard surrounds the home, with trees lining the background under a partly cloudy sky.

Flat in Crown Point

Lovely 2 bedroom just a few blocks from the square

6 Minute's walk from The Square! Shopping, dining, and sightseeing in the historical Crown Point Courthouse Square. Your family will be close to everything when you stay at this centrally-located place. Welcome to this amazing Century old freshly redone duplex home. You will be so very relaxed as you walk through the large shared front porch with 2 cozy reading nooks and upstairs into your private snug spot to lay your head while you're in Crown Point.

4.85 out of 5 average rating, 164 reviews

A well-appointed bedroom features a spacious bed adorned with a soft blush and white blanket. A bedside lamp and decorative elements are present. Natural light filters through a window dressed with sheer curtains, creating a cozy ambiance. A small chair complements the interior design.

Flat in Hammond

Plant MOOD FREE Wi-fi, parking, washer & dryer!

LATE CHECK-IN guest are welcome!!!! PLEASE READ MY FULL AIRBNB LISTING PRIOR TO BOOKINGS!!!! This special place is close to everything, making it easy to plan your visit. • I80, 294, 94 highways/tolls, etc. • Chicago • Shopping galore • A fun array of restaurants AND A LOT OF FREE PARKING!!! I’m extremely close to MUNSTER, HIGHLAND, SCHERERVILLE, DYER and many more Indiana locations! I’m extremely close to LYNWOOD, LANSING, CALUMET CITY, and many more!

4.99 out of 5 average rating, 256 reviews

Flat in Lower West Side

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

4.86 out of 5 average rating, 124 reviews

A cozy seating area is presented, featuring a dark couch with a single orange cushion and a small round table beside it. A pink armchair with decorative pillows adds a touch of color. Wall decor includes welcoming signs and art pieces, creating a homey ambiance.

Flat in Valparaiso

Cute Skylar: Valparaiso University ShortTerm Stays

Welcome to Skylar's Relaxing Spot! This cozy one-bedroom on the second level features a queen-size bed, its own entrance, deck space, and building laundry facilities. Perfect for accessing downtown and Valpo University. Enjoy strong WiFi for remote work and relaxing movie nights on the TV. Located near Route 30 and I-49, it’s an hour from Chicago and 15 minutes from Indiana Dunes, close to malls, ice cream parlors, and great restaurants! ☺️

4.8 out of 5 average rating, 145 reviews

Midtown Apt 1 Bed, 1 Sleeper Couch Upstairs Apt

This property has about 20 stairs to get to the apartment above a State Farm office. Close to downtown, 2.0 miles to Washington Park & Beach at Lake Michigan, 2.0 miles to Blue Chip Casino and 1.1 miles to the Lighthouse Outlet Mall. There is the South Shore train station 0.7 of a mile away. That train can take you to Chicago, Illinois or to South Bend, Indiana. Amtrak is 1.5 miles away. Michigan City Marina or Zoo are 2.0 miles away.

Popular amenities for Gary apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

5 out of 5 average rating, 65 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

4.74 out of 5 average rating, 19 reviews

A bright studio features a spacious bed with light bedding and two bedside lamps. A kitchenette with white cabinetry is visible in the background, along with a dining table for two. Large windows are framed by dark curtains, enhancing the natural light.

Flat in Hyde Park

Sunny Studio by UChicago, Walk to Campus & Museums

4.91 out of 5 average rating, 93 reviews

A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.

Flat in Homewood

Charming Garden Apartment

4.93 out of 5 average rating, 15 reviews

A bright living area is highlighted by a large television with a wildlife scene displayed. A modern chair sits next to a wooden media console. A small workspace with a desk and chair is visible, surrounded by greenery from nearby plants and natural light.

Flat in Whiting

The Beach Loft

4.94 out of 5 average rating, 81 reviews

A bright living area features large windows allowing natural light to fill the space. A light brown leather sofa and a cozy armchair are accompanied by a wooden coffee table. A decorative rug adds warmth, while shelves with potted plants and books enhance the inviting atmosphere.

Flat in Little Village

Flor de Luna ~ Little Village Chicago Retreat

4.83 out of 5 average rating, 6 reviews

The inviting living area features a comfortable sofa arranged in front of a wall-mounted television, with large windows allowing natural light. Soft neutral tones dominate the decor, creating a relaxed ambiance within the space.

Flat in Valparaiso

Creekside Cozy 3BD • Near Dunes

4.92 out of 5 average rating, 86 reviews

A well-arranged living space features a spacious bed covered with a light grey blanket. A modern couch in a dark hue is situated near the wall, complemented by colorful wall art above. Natural light filters in through a nearby window, enhancing the inviting atmosphere.

Flat in Uptown

Private studio near Wrigley

4.97 out of 5 average rating, 69 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

4.94 out of 5 average rating, 183 reviews

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.

Flat in Oak Park

A Quiet Stay While You Are Away Oak Park

4.83 out of 5 average rating, 363 reviews

A modern kitchen area features a compact island with a sleek sink and metallic fixtures. A round dining table with black-and-white polka dot chairs sits against a light pink floral accent wall. Warm lighting enhances the inviting ambience of the space.

Flat in West Town

*Entire City Apartment 1 block to Train Park Free

4.91 out of 5 average rating, 197 reviews

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.

Flat in Oak Park

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

4.94 out of 5 average rating, 308 reviews

A cozy living area is featured with two large windows allowing natural light to fill the space. A hanging chair adds a unique touch, while a dark sofa and a coffee table sit on a patterned rug. A television is positioned on a stand nearby.

Flat in Blue Island

Charming Unique 2 Bdrm Apartment in Victorian Home

4.86 out of 5 average rating, 222 reviews

The living area is furnished with a comfortable gray sofa and a glass coffee table, complemented by decorative pillows. A large wall art piece depicting a city skyline adds a modern touch. Natural light fills the space, enhanced by nearby windows and an indoor plant.

Flat in Forest Park

2 Bed Apartment | Convenient Access to Downtown

5 out of 5 average rating, 287 reviews

A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.

Flat in Lincoln Park

Explore Lincoln Park from a Polished Apartment

4.85 out of 5 average rating, 309 reviews

A cozy living area features a dark leather couch adorned with a decorative pillow, complemented by a wooden rocking chair. Two glass-topped tables rest on a patterned area rug, while natural light enters through a pair of windows dressed with blinds.

Flat in Oak Park

Cozy and Character-Rich Chicago Style, Tv 42-2

4.99 out of 5 average rating, 137 reviews

A modern kitchen and dining area are highlighted by sleek white cabinetry and stainless steel appliances. A spacious island with two stools provides seating, while a wooden dining table accommodates four. A decorative shelving unit displays various items, enhancing the clean aesthetic.

Flat in Lincoln Park

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Apartment rentals with a hot tub

4.8 out of 5 average rating, 115 reviews

An inviting backyard features a central fire pit surrounded by several metal chairs. The bi-level house is visible in the background, with large windows reflecting the evening light. A hot tub is seen nearby, framed by trees and a spacious lawn.

Flat in Bridgman

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

A door labeled 'Suite 3' opens to a bright, airy loft space. Soft yellow curtains frame a window, and a spacious bed with white linens is centered towards the back. A rattan coffee table is positioned in the foreground, surrounded by comfortable seating.

4.96 out of 5 average rating, 47 reviews

Romantic Couples LOFT- King Bd, Hot Tub, Fire Pit

4.84 out of 5 average rating, 104 reviews

A modern living area features a light-colored sofa adorned with decorative pillows, set against large floor-to-ceiling windows that offer views of the city skyline. A textured area rug defines the space, while a coffee table displays artfully arranged decorative items. A dining table with black chairs completes the setting.

Flat in West Loop

Top Floor Views + Central Comfort

4.85 out of 5 average rating, 95 reviews

An open-concept living and dining area is showcased with a gray sectional sofa and a wooden coffee table. A modern ceiling fan hangs above, and natural light fills the space. A dining table with six chairs is positioned nearby, adjacent to a sleek kitchen.

Flat in East Rogers Park

Spacious Beautiful Condo

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, 141 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

4.89 out of 5 average rating, 302 reviews

Flat in Sawyer

Cozy Cottage by Lake MI&Dunes w/ private Hot Tub!