Apartment holiday rentals in Gary

4.85 out of 5 average rating, 151 reviews

A modern living area features a sleek black sofa paired with two cozy white armchairs. Natural light pours in through large windows adorned with light grey curtains. Minimalist decor includes two framed artworks and a small wooden side table that complements the space.

Flat in Berwyn

2 bedroom• 3 beds • 1 bath Apartment in Berwyn

Enjoy a stylish and elegant experience at this centrally-located private apartment On famous Route 66. Sunny, clutter free very spacious 2nd floor. Apt. Can sleep upto 6 ppl. Inflatable bed added for extra sleep option. Prepped for photo sessions of your own. •Restaurants, Auto repair shops and Walgreens are walking distance and much more. •Metra is a 10-15 minute walk. •DT Chicago 18 min •Brookfield Zoo 15 min Away •Midway Airport 15 min •O’Hare Airport 30 min •Mall 10 min •Loyola Hospital

4.85 out of 5 average rating, 176 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

1Plant MOOD FREE Wi-Fi Street Parking Washer/Dryer

PLEASE READ THE ENTIRE LISTING BEFORE BOOKING! LATE CHECKINS! Enjoy FREE Washer/Dryer Full Kitchen/STREET PARKING! 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 Illinois locations!

4.99 out of 5 average rating, 174 reviews

A bright living room is showcased with large windows allowing natural light to fill the space. A plush beige sofa is paired with two striped armchairs, accented by decorative cushions. A white coffee table rests on a textured area rug, enhancing the room's warm atmosphere.

Flat in Valparaiso

ValpoVilla: Location, location, location!

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!

4.87 out of 5 average rating, 744 reviews

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.

Flat in Oak Park

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

4.95 out of 5 average rating, 249 reviews

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

Flat in Roscoe Village

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

4.93 out of 5 average rating, 111 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

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

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.

4.95 out of 5 average rating, 112 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!

4.94 out of 5 average rating, 192 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

Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

4.94 out of 5 average rating, 124 reviews

A bright and airy loft space is characterized by sloped ceilings and wooden paneling. A dark sofa is complemented by decorative pillows, while a small desk and chair are positioned by the window. Lush greenery adds a touch of nature to the cozy setting.

Flat in Archer Heights

Comfortable and Cozy Apartment

Enjoy this simple and cozy apartment! Located just a few blocks from stores like Walgreens, Aldi, Target, Laundromat and various restaurants. Its conveniently located just a 10 minute walk from the orange line cta train station. Disfrutá de la sencillez de este alojamiento tranquilo y céntrico. Ubicada a dos minutos de tiendas como target, Walgreens, Aldi, Lavandería y restaurantes . Estamos a 10 minutos del aeropuerto midway y 15 minutos del centro de Chicago.

4.94 out of 5 average rating, 130 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.

4.94 out of 5 average rating, 558 reviews

A sunroom is filled with natural light, featuring large picture windows offering leafy views. Two rattan chairs, adorned with cushions, face a wooden table. A decorative lamp stands nearby, with vintage touches enhancing the relaxed ambiance of the space.

Flat in Sawyer

Cozy Chalet by Lake MI&Dunes with Fire Pit

Sawyer Gem: Cozy Vintage Retreat Near Lake & Dunes! Charming vintage chalet sleeps 4 . Sun-drenched sunroom, private fire pit. Walk to restaurants, bars, antiques. Minutes to Lake Michigan & Warren Dunes. Adding to its unique charm, The Cozy Chalet is directly connected to Harbor Country Mission, a wonderful antique shop supporting the local community. You'll enjoy a separate entrance for complete privacy and convenience. Book your stay today!

4.82 out of 5 average rating, 254 reviews

A bright red sofa is positioned against a light-colored wall, accompanied by a small side table that holds a decorative bowl. A colorful woven blanket is draped over the arm of the sofa. Natural light enters through a small window, enhancing the warm atmosphere.

Flat in Gary

Miller Beach Retreat

This Airbnb experience, situated by the best place to be in Indiana, will surely fulfill any travelers desires. Guests will be surrounded by lush forest and just a 200 steps walk from the beautiful beach. Which on any given day, is bound to be completely empty. Rest at this gorgeous home, bountiful forest, and tranquil beach, and become truly at peace. Embark on the serenest place to be in Indiana, The Gary Miller Beach Retreat.

Popular amenities for Gary apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.97 out of 5 average rating, 137 reviews

A light-filled living area features a black leather sofa with decorative pillows and a wooden coffee table. Natural light enters through large sliding glass doors that open to a balcony, offering views of the outdoors. A circular woven pouf adds textural contrast to the floor.

Flat in Saint Joseph

Luxury Waterfront Condo

4.93 out of 5 average rating, 41 reviews

The entrance features a wrought iron railing adorned with lush green vines, creating a natural frame. A decorative lantern is mounted on the wall beside an inviting wooden door with intricate design, enhancing the home's welcoming appearance.

Flat in Gary

Quiet retreat near hiking and beach

4.79 out of 5 average rating, 29 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/25 minutes to Chicago Navy Pier

4.72 out of 5 average rating, 64 reviews

A charming vintage building features a striking blue entrance door framed by vibrant autumn foliage. The stone façade is complemented by green climbing vines and a small patio area with a bench, enhancing the inviting exterior.

Flat in Gary

French château -literally 150 steps from BEACH

5 out of 5 average rating, 307 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

4.96 out of 5 average rating, 297 reviews

The living area features a spacious sectional sofa and a coffee table at its center. A TV is positioned against a light-colored wall, while a dining space can be seen in the background with a small table and chairs. Natural light is welcomed through multiple windows.

Flat in Evanston

Stylish & Comfy Gem near Downtown~Balcony~Parking

4.53 out of 5 average rating, 17 reviews

Flat in Munster

Cozy Modern Retreat - Home Away from Home

4.86 out of 5 average rating, 365 reviews

A spacious living area features a modern sectional sofa in neutral tones. A sleek television is mounted on the wall opposite a minimalist coffee table. The adjoining dining area, visible through an archway, includes a round table with four chairs.

Flat in Forest Park

Home in Forest Park Upstairs.

Private apartment rentals

4.95 out of 5 average rating, 19 reviews

Beachside Top-Floor Apt | Steps to Lake Michigan

4.96 out of 5 average rating, 51 reviews

A comfortable seating area features a plush sectional sofa adorned with soft throw pillows. Light beige cushions contrast against the deep green walls. A large television is mounted opposite the seating, while sheer curtains frame the window beside a door that leads outside.

Flat in Bridgeport

Designer Garden Unit in Bridgeport

5 out of 5 average rating, 13 reviews

A spacious loft area features a comfortable king-size bed and a cozy sofa, complemented by a vintage armchair. The space is decorated with wooden beams and rustic accents, with soft lighting illuminating the neutral color palette. A large window allows natural light to fill the room.

Flat in Westville

Vintage Store Loft Stay on a Rescue Farm

4.94 out of 5 average rating, 49 reviews

A spacious living area features high ceilings with a skylight and large windows, offering ample natural light. A comfortable green sofa and a black armchair are positioned near a coffee table. A fireplace and a television are visible, with scenic views seen through the glass doors.

Flat in South Side

Sunny Penthouse - Oakwood Beach

4.98 out of 5 average rating, 55 reviews

A two-story black exterior home features large front windows and a decorative door with a circular window. The entrance is approached by stone steps leading to a small garden area with a fountain and landscaped greenery, framed by a well-maintained lawn.

Flat in Whiting

The Standard- 1st floor

4.79 out of 5 average rating, 28 reviews

A spacious living area features a large sectional sofa in a rich brown hue, providing ample seating. A 65-inch smart TV is positioned on a light-colored media console. Natural light enters through two windows, and a decorative mirror is visible on the wall.

Flat in Hobart

Downtown Hobart 1BR | Parking + Wi-Fi Workspace

A charming blue house with a welcoming front porch is displayed, featuring a newly painted exterior. Colorful flowers and pumpkins are placed on the porch steps, while a friendly scarecrow adds a festive touch. Lush green grass surrounds the home, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 93 reviews

King Bed Retreat, Minutes to Beach & Dunes

A comfortable seating area is showcased, featuring a dark blue sectional couch adorned with patterned throw pillows. A small black table sits in front, complemented by a decorative plant. Natural light enters through a window, with soft gray curtains framing the view.

4.85 out of 5 average rating, 41 reviews

Midtown Upstairs Apt one bed and one sleeper couch

Apartment rentals with a hot tub

4.81 out of 5 average rating, 122 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, 55 reviews

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

4.86 out of 5 average rating, 121 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

4.76 out of 5 average rating, 106 reviews

Flat in Vittum Park

Super Paradise+65 Amenities*Downtown 15 Min

4.65 out of 5 average rating, 31 reviews

A spacious bedroom with large windows provides an expansive view of the city skyline. The comfortable bed is flanked by bedside tables with lamps, and art pieces are displayed on the wall. Natural light brightens the room, enhancing its modern aesthetic.

Flat in West Loop

Level One Bedroom Suite | Fulton Market

4.9 out of 5 average rating, 60 reviews

Flat in Chicago

Spacious 1BR | 1 Garage Parking | Nightlife nearby

4.92 out of 5 average rating, 167 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