Holiday rentals in Bridgeport

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Top-rated holiday rentals in Bridgeport

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Guest favourite
A spacious living area features a gray sectional sofa with a light green throw draped over the arm. A large area rug in soft gray covers the hardwood floor, while natural light streams through multiple windows with blinds.
Home in Bridgeport
4.78 out of 5 average rating, 177 reviews

Golden Colonial Home

You will be close to everything when you stay at this centrally-located place. The street is full of life and sometimes noisy. We are minutes away from Seaside Park Beach, Jennings Beach and Saint Mary’s by the Sea. You can make your way to any of our local fishing piers for the best fishing experience in the NorthEast. Our Downtown area is 5 minute drive and it’s full of night life and restaurants. We also have local farms near by great seasonal fruit) depending on the season. Beautiful trails.

Top guest favourite
The kitchen features modern cabinetry with a contrasting dark granite island. Three cushioned stools are positioned at the island. Natural light enters through a window above the sink, illuminating new stainless steel appliances and a sleek backsplash. A door leads to the outdoor area.
Home in Black Rock
4.97 out of 5 average rating, 101 reviews

Cape on the Water

Welcome to our Cape on the Water! This unique property is located on beautiful Ash Creek, an inlet off Long Island Sound offering views of tidal wetlands, including tons of fish, bird, kayakers, paddle boarders, small sail boats etc. The house is a newly renovated Cape Cod with open floor concepts, updated Kitchen and bath rooms. Refinished oak hardwood floors through out the entire house. Brand new large deck. The house has a very cozy feel and has been also updated with brand new HVAC system.

Top guest favourite
An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.
Flat in Milford
4.97 out of 5 average rating, 618 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Top guest favourite
Flat in Fairfield
5 out of 5 average rating, 69 reviews

New & Modern Studio Apartment in Fairfield CT

This newly reconstructed downstairs stylish, modern, and spacious studio features a queen bed & a queen pull-out sofabed with remote lighting, luxe bathroom with towels and refillables, a fully loaded sleek kitchen, a 70” TV with surround sound, and guest-controlled ambient lighting. Enjoy a private entrance, in-suite laundry, guest-controlled heat, and ceiling fan. Close to Fairfield & Sacred Heart Universities, shops, beach, and quick NYC transit. Comfort and convenience in one chic space!

Top guest favourite
A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.
Home in Milford
4.99 out of 5 average rating, 162 reviews

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

Superhost
Guest suite in Fairfield
4.88 out of 5 average rating, 128 reviews

Fairfield 2nd Floor · 2 Rms · Full Bath · Parking

ENTIRE 2nd FL for up to 2️⃣ adult guests ONLY 2️⃣ Rooms➕Skylit Full Bathroom Exclusive Driveway Parking➕locked entrance leading airbnb, separate from full-time renters on 1st FL Heat & Cool: wall-mounted AC➕portable Dyson ➕ Central AC w/2 sensors - host adjustable remotely TV is Screen only, works with Bluetooth & Chromecast, NO Services Kitchenette: heat/store food (NO cooking), allows affordable stay in affluent Fairfield Town Professional Clean Service Host Assistance Virtually

Guest favourite
The studio features a neatly arranged sleeping area with a quilted bedspread in blue and white patterns. A desk with a chair is positioned nearby, allowing for a focused workspace. Natural light streams through sheer curtains, creating a bright and welcoming ambiance.
Home in Bridgeport
4.93 out of 5 average rating, 73 reviews

Cozy Studio in Bridgeport

Charming and fully equipped studio located in the heart of Bridgeport. Perfect for business travelers, couples, or solo adventurers, this cozy retreat features a comfortable bed, high-speed Wi-Fi, a private entrance, and a fully stocked kitchen for your convenience. Enjoy easy access to local restaurants, cafes, and shops, as well as public transportation and major highways. Whether you’re here for work or leisure, this studio offers everything you need for a relaxing and stress-free stay

Superhost
A bright living area features two plush sofas, one in a muted beige and the other in a deep blue, positioned around a circular wooden coffee table. Light-colored curtains adorned with a coral pattern frame the windows, while shelves on the walls display decorative items.
Home in North End
4.94 out of 5 average rating, 143 reviews

Families|Charming |King Bed| Near SHU

Welcome to our updated and inviting nautical-themed residence. The home is located close to the University of Bridgeport, Sacred Hearth University and St Vincents Hospital. Enjoy the excitement of the ambiance around the fire pit in the private backyard and a grill for cooking, and the convenience of all of the amenities in the home. Guests can truly relax and make the most of their time in our tranquil setting. There is a dedicated workspace for remote workers and is family friendly.

Guest favourite
A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.
Cottage in Milford
4.94 out of 5 average rating, 378 reviews

Spring Sale! CozyCottage/Pet-friendly/WalktoBeach

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Top guest favourite
The bedroom features a queen size spindle bed with quality bedding, flanked by two nightstands with lamps. A dedicated work desk is equipped with a lamp and USB ports. Shelving adds storage, while a small seating area is present, illuminated by natural light from the windows.
Flat in Fairfield
4.98 out of 5 average rating, 166 reviews

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

Superhost
A cozy living area features a dark, comfortable couch and a decorative rug. A wall-mounted television is positioned above a simple mantel with a potted plant. Natural light filters through floral curtains, illuminating a wooden desk and chair against the wall.
Flat in South End
4.89 out of 5 average rating, 119 reviews

Seaside Studio in Historic Bridgeport Brownstone

Keep it simple at this peaceful and centrally-located historic brownstone built by P.T. Barnum for his staff 140 years ago. Basement unit across the street from Bridgeport University, 1 block to Seaside Park and beaches, 5 min walk to amphitheater, and 10 min walk to Metro North or LI ferry. Includes kitchenette with fridge/freezer, microwave, stove and oven, desk, couch, wifi, tv with Roku , iron, hairdryer, and full bathroom.

Top guest favourite
Home in Fairfield
4.96 out of 5 average rating, 200 reviews

Cozy Cottage with Fire Pit, near Beach

Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities for an unforgettable stay.

Popular amenities for Bridgeport holiday rentals

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Frequently Asked Questions

  • How much does it cost to stay in apartment rentals in Bridgeport?

    Experience the best of Bridgeport with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Bridgeport?

    Yes! Work meets play with ease at over 100 house rentals in Bridgeport featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Bridgeport?

    Make yourself at home in Bridgeport by choosing from our most frequently booked neighborhoods. We have over 400 vacation rentals in Seaside Park, over 490 vacation rentals in Steel Point, and over 400 vacation rentals in Black Rock.

  • Are there family-friendly house rentals in Bridgeport?

    Bridgeport has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly apartment rentals in Bridgeport?

    Four-legged friends are welcome in Bridgeport. Choose from more than 30 apartment rentals for guests traveling with pets.

  • Are there Bridgeport vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Bridgeport, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Bridgeport have air conditioning?

    Absolutely! We offer over 90 apartment rentals with air conditioning in Bridgeport. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Bridgeport have wifi?

    Absolutely! We offer over 160 house rentals with wifi in Bridgeport. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Bridgeport have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Bridgeport. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Bridgeport have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Bridgeport. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Bridgeport

  • Total holiday rentals

    Explore 320 holiday rentals in Bridgeport

  • Nightly prices starting at

    Bridgeport holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 7,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    140 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 80 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wifi availability

    310 of Bridgeport holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Bridgeport rentals

  • 4.7 Average rating

    Bridgeport stays receive an average rating of 4.7 out of 5 from guests