Apartment holiday rentals in Valparaiso

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.

4.93 out of 5 average rating, 138 reviews

A cozy living space features a light-colored sofa with decorative pillows, accompanied by an accent chair in blue. A small coffee table sits in front, and a kitchen area with white cabinetry is visible in the background. Natural light enters through large windows, illuminating the warm wood flooring.

Flat in Valparaiso

Downtown Apartment on Lincolnway

Convenience at its best meets historic charm! Located in the center of downtown Valparaiso (literally), The Lincoln is in a prime location that puts you within minutes to enjoy all that downtown Valparaiso and the surrounding areas have to offer. Walk to fabulous restaurants, local boutique shops, bars, breweries, wineries, and distillery in minutes. Downtown Valpo offers numerous exciting events throughout the year. The Lincoln is perfect for families & friends who want to relax or adventure!

A cozy living area features a comfortable sofa paired with wooden side tables. A dining table is set for four, positioned near large windows that invite natural light. Decorative items and books are arranged on the coffee table, enhancing the room's inviting ambiance.

4.96 out of 5 average rating, 151 reviews

Heart of Historical Dist.*King*Parking*A/C*#1

Our charming one bedroom 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.

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!

4.8 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

Welcome to "Lake 2 Grapes" Bridgman is a little gem located between St. Joe and Warren Dunes. Minutes to Lake Mi. beaches, craft breweries, and wine trails. Relax in the upper level of our bi-level vacation home w/private entrance. This 3 bedroom, 2 bath includes a beautiful Master suite! Enjoy the Hot tub and fire pit in the backyard. Wine Tour? Stay with us and you'll receive a discount with "Grape & Grain Tours" plus complimentary pick up and drop off. Must be 25 or older to book.

4.83 out of 5 average rating, 362 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

Perfectly private - large & comfortable with full kitchen. FREE & EASY street parking One block to (Green Line) train stop to United Center - Concerts, Bulls & Blackhawk games. Two stops to trendy West Loop Randolph bars, restaurants and shops. 10 minute ride downtown Chicago. Kitchen has cooking utensils & coffee, cream, sugar, spices. Shampoo/conditioner/towels/linens are provided. Free wifi. PLEASE NOTE No visitors No smokers no exceptions and agree per message to confirm reservation

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!

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.

4.85 out of 5 average rating, 311 reviews

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.

4.94 out of 5 average rating, 121 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.

4.99 out of 5 average rating, 256 reviews

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, 144 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 Valparaiso apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.89 out of 5 average rating, 54 reviews

An open living area showcases a comfortable sofa in warm tones, complemented by a classic arcade machine featuring Pac-Man. The kitchen is equipped with modern appliances and sleek cabinetry. A cozy sleeping space is featured, with soft linens and stylish decor creating a welcoming environment.

Flat in Little Village

10 Mins to Downtown Luxurious Cozy Boho Sleeps 5

4.91 out of 5 average rating, 87 reviews

A welcoming entrance is framed by a well-maintained garden pathway leading to a wooden door with a decorative awning. Potted plants and colorful flowers on either side enhance the entry, creating an inviting first impression.

Flat in Chatham

Carol’s Guesthouse: Your Needs Are Covered!

5 out of 5 average rating, 8 reviews

An open-concept living area features large windows allowing natural light to fill the space. A modern sofa is arranged around a glass coffee table, enhancing the contemporary design. A flat-screen TV is mounted on the wall, providing entertainment options.

Flat in Tri-Taylor

New Build in Pilsen! Spacious 2 Bed 2 Bath Unit

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

A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.

4.94 out of 5 average rating, 79 reviews

Pilsen Modern Chic Retreat

4.94 out of 5 average rating, 16 reviews

The modern kitchen features white cabinetry with marble countertops and stainless steel appliances. A window allows natural light to brighten the space, which includes a sink and a gas stove. Kitchen utensils and a dish rack are neatly organized within arm's reach.

Flat in Steger

Private Deluxe Apartment Clean, Safe & Affordable

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

4.74 out of 5 average rating, 341 reviews

A bright living space features a dark brown sofa adorned with orange cushions. A stylish coffee table sits on a patterned area rug, while two large windows allow natural light to fill the room. A corner mirror reflects the sofa and a cozy bed is visible in the background.

Flat in Bridgeport

Bright & Spacious| Free Parking |Trendy Bridgeport

Private apartment rentals

4.9 out of 5 average rating, 435 reviews

A bright living area features a comfortable gray sofa with decorative pillows, paired with two teal chairs. A mirrored wall accent adds depth, while a large flat-screen TV is mounted nearby. A coffee table with a zigzag area rug enhances the inviting space.

Flat in Roscoe Village

Relax and Enjoy Chicago in an Updated and Private Apartment in Roscoe Village

A modern kitchen features sleek black cabinetry and appliances, complemented by a contrasting white countertop. Stylish stools are arranged around a small kitchen island. The wall is adorned with a framed painting, while decorative items are displayed on open shelves above the countertop.

4.87 out of 5 average rating, 292 reviews

Spectacular Pilsen Studio for 2!

5 out of 5 average rating, 118 reviews

An open-concept living area is visible, featuring a modern kitchen with stainless steel appliances, including a refrigerator. A cozy seating area contains a sofa, and a dining table with yellow chairs is positioned in front of a window, providing ample natural light.

Flat in Logan Square

Logan Square Cozy 2BR Basement Apartment

4.82 out of 5 average rating, 463 reviews

The image displays an advertisement featuring the text 'Western Avenue Lofts + Studios' in bold letters. Below it, details regarding artist studios and loft availability are presented. An artistic design element, representative of the historical context, is visible in the background.

Flat in Wicker Park

WESTERN AVE ARTISTS LOFTS- Park Free

4.77 out of 5 average rating, 557 reviews

A modern living area features a green velvet couch paired with two sleek white chairs. A round coffee table sits in the center, accented by decorative items. Artwork with a geometric pattern adorns the wall, complemented by a contemporary floor lamp.

Flat in Logan Square

Clean & Bright Chicago Condo - FREE Parking Spot

4.98 out of 5 average rating, 179 reviews

The bedroom is designed with a spacious bed centered against an accent wall featuring geometric patterns. A plush bench is positioned at the foot of the bed. Warm lighting illuminates the room, complemented by rich curtains and wooden flooring.

Flat in Magnificent Mile

Elegant Suite in Gold Coast

4.9 out of 5 average rating, 193 reviews

A spacious living area features a light-colored sofa and a dark wood coffee table, surrounded by large windows that allow ample natural light. Decorative plants are placed around the room, and a brick fireplace adds a focal point, complemented by framed artwork on the walls.

Flat in Albany Park

Huge Pet Friendly East Albany Park Apartment

4.94 out of 5 average rating, 102 reviews

The spacious garden studio features a cozy living area with a textured sofa adorned with decorative pillows. A stylish coffee table is positioned in front, complementing an adjacent dining area. The kitchenette showcases modern appliances, while warm lighting enhances the welcoming ambiance.

Flat in Edgewater

Edgewater Studio on Paulina

Apartment rentals with a hot tub

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

4.97 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

4.93 out of 5 average rating, 374 reviews

Flat in Sawyer

Cozy Mid-Century Mod By Lake MI&Dunes with Hot Tub

5 out of 5 average rating, 5 reviews

Flat in West Town

Modern 4BR Retreat in Vibrant West Town

A well-appointed hot tub with a rich wooden exterior is positioned on a deck, offering views of the expansive water and surrounding greenery. The serene landscape is complemented by a clear blue sky, enhancing the inviting outdoor space.

4.78 out of 5 average rating, 98 reviews

HotTub/Beachfront/Steam/Gameroom/Pets/MassageChair

4.97 out of 5 average rating, 32 reviews

An indoor swimming pool is featured, with clear water reflecting natural light from large windows. The area includes lounge chairs alongside the pool, and minimalistic decor enhances the spacious environment. Black and white tiles line the edges, contributing to a modern aesthetic.

Flat in South Loop

The Parkside Panorama