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Apartment holiday rentals in Bridgeport

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Bridgeport

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Top guest favourite
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
5 out of 5 average rating, 296 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Guest favourite
A modern living area features a grey sectional sofa and a light-colored armchair positioned around a soft area rug. Two windows allow natural light to enter, and wall art decorates the walls. Steps lead to an upper level, contributing to an open and inviting layout.
Flat in Avondale
4.94 out of 5 average rating, 108 reviews

Best Deal in Chicago | Great Food & Free Parking

Clean & modern Avondale apt close to Blue Line, perfect for urban explorers! Stylish decor, comfy bed, and a cozy ambiance await. Explore nearby cafes, bars, and boutiques, or hop on the train for downtown adventures. Easy to access & great neighborhood. Easy permit parking (free passes provided) on street allows for the ability to drive or take public transportation wherever you want to explore. Avondale has been voted one of the best neighborhoods in Chicago! Come see what the fuss is about.

Guest favourite
A comfortable living room features a vibrant orange sofa, complemented by a glass coffee table and a patterned area rug. Potted plants provide greenery, while light fixtures add warmth to the space. Two additional seating options are included, creating an inviting atmosphere.
Flat in Little Village
4.91 out of 5 average rating, 234 reviews

Fairfield Flat, Airy Vintage Rehab

This remodeled first floor apartment is close to the California Pink Line Station, Pete's Fresh Market, and Douglass Park. Pilsen and West Loop night life a short train ride away. Situated in a quiet corner of Little Village, our neighborhood of predominately Mexican and Black multi-generational families is teeming with tamale stands, paleta vendors, and children playing. Great for couples or friends, though parents have expressed frustration with the hard, or uneven surfaces, and the stairs.

Guest favourite
A comfortable living area is highlighted by a light gray sectional sofa and a white coffee table, placed on a textured gray rug. The kitchen area is visible in the background, featuring wood cabinets and modern appliances, enhancing the space's functionality.
Flat in Bridgeport
4.93 out of 5 average rating, 111 reviews

Prime Bridgeport – McGuane Park

Located by Halsted Orange Line in Bridgeport, our Airbnb has is CENTERED around all the action in the neighborhood; surrounded by Grocery Stores, Fast Food, Drug Stores, Restaurants, and Iconic Parks. With a short commute to the Loop, UIC, Chinatown, we are especially sustainable for longer-term tenants! Enjoy the luxury of firm memory-foam mattresses and pillows and High-speed Internet, Central Heat and A/C and unlimited complimentary coffee for an amazing stay! 1 Queen Bed 1 Full Bed

Guest favourite
A colorful mural featuring a heart symbol is prominently displayed. The heart is surrounded by a sunburst pattern and flanked by vibrant decorative elements in various colors. The word 'PILSEN' is written across the heart in a bold font, emphasizing the community's identity.
Flat in Lower West Side
4.85 out of 5 average rating, 208 reviews

Downtown & UC Nearby · Transit at Your Door

•Steps from the Damen Pink Line •Minutes to downtown Chicago via car or train •Easy access to major expressways I‑290 and I‑55 •Near major attractions like the United Center/Chinatown/Greektown/UIC/ West Loops nightlife and the Medical District •Vibrant cultural neighborhood - experience Pilsen’s rich art scene and authentic local dining •Ceiling height approx. 6’3” - please keep in mind when reserving •Memory Foam mattress •Guests must be 25+, have a verified account, and positive reviews

Guest favourite
The living area is furnished with a gray sofa adorned with patterned cushions, positioned next to a natural wood coffee table. A potted plant and a decorative mirror enhance the space. Two windows allow natural light to brighten the room.
Flat in Lower West Side
4.94 out of 5 average rating, 177 reviews

Cute, Clean, Cozy Apartment in Pilsen

Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

Top guest favourite
A bright hallway is illuminated by natural light, showcasing a mix of art and plants. Shelves with various glassware and plants line one wall, while framed artwork featuring mountains and landscapes adds character. Light wooden flooring runs throughout the space.
Flat in Humboldt Park
4.99 out of 5 average rating, 162 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Top guest favourite
A welcoming living space features a blend of modern and natural elements. A green accent wall provides a backdrop to a cozy seating area with black chairs and a sofa. Decorative plants are placed throughout, enhancing the bright and open atmosphere.
Flat in Ukrainian Village
4.99 out of 5 average rating, 213 reviews

Bright Cozy Modern-Chic Condo in Trendy West Town

Kick back & relax in your home away from home in our luxurious, spacious and peaceful abode in the heart of the West Town & Noble Square neighborhoods, close to downtown. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Grand Avenue, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Top guest favourite
The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.
Flat in Noble Square
4.97 out of 5 average rating, 580 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Guest favourite
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
4.84 out of 5 average rating, 321 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.

Guest favourite
A comfortable bedroom features a spacious bed adorned with patterned pillows and a cozy blanket. Two bedside lamps provide soft lighting, while a decorative bicycle wall piece is displayed above the bed. Floor-to-ceiling curtains frame a window, allowing natural light to fill the room.
Flat in Bridgeport
4.85 out of 5 average rating, 110 reviews

WF Home Sweet Home

Located in the center of the Bridgeport area, This AirBnB is clean, tidy, cozy and comfortable. It's the first choice for visitors. Two minutes walk to 8 and 31 bus stop, 15 minutes drive to downtown, McComick Place, and it close to Chinatown and White Sox Field. In addition, you can enjoy a variety of cuisines in a few minutes' walk, including Chinese, Japanese, Korean, Mexican restaurant, Starbucks,McDonald's, Dunkin Donuts, CVS. Warmly welcome friends from all over the world

Guest favourite
A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.
Flat in Bridgeport
4.93 out of 5 average rating, 191 reviews

Blue Brick Apartment in Bridgeport - Park for Free

• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

Popular amenities for Bridgeport apartment rentals

When is the best time to visit Bridgeport?

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Avg. price$113 SGD$100 SGD$126 SGD$134 SGD$145 SGD$150 SGD$158 SGD$148 SGD$131 SGD$131 SGD$125 SGD$122 SGD
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Quick stats about flat rentals in Bridgeport

  • Total holiday rentals

    Explore 90 holiday rentals in Bridgeport

  • Nightly prices starting at

    Bridgeport holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,900 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    80 of Bridgeport holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Bridgeport rentals

  • 4.6 Average rating

    Bridgeport stays receive an average rating of 4.6 out of 5 from guests

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