Holiday rentals in Bridgeport

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Top-rated holiday rentals in Bridgeport

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

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Top guest favourite
The spacious living area features a large window allowing natural light to fill the room. A comfortable seating arrangement includes a plush armchair and a sofa, accompanied by a coffee table. Decorative plants and a decorative rug complement the elegant furnishings, including a classic wooden armoire.
Guest suite in Fairfield
4.96 out of 5 average rating, 243 reviews

2 BRm Suite; Ktchn; Livng area; wash/dryr; Private

Fully accessorized, large (919 sq ft) beautiful suburban space with bedroom (queen); convertible Murphy bed (queen), in-room sitting area/large screen TV, kitchenette; 2nd room: bedroom (queen) with living space / large screen TV; private full bath; in-suite washer/dryer; private entry to suite (front door; up 1 flight of stairs). Includes light continental breakfast. Owners on property. Off street parking. Train station a mile away (NYC: 70 min). 2 miles to beach. Easy walk to Fairfield U.

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.

Guest favourite
A spacious bedroom features a king bed with a soft green duvet and decorative pillows. Two nightstands with lamps are positioned on either side. Natural light enters through two windows adorned with bamboo shades. A framed coastal artwork is displayed above the headboard.
Guest suite in Fairfield
4.93 out of 5 average rating, 186 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

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, 617 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
The living area features a blend of classic and modern decor, including a comfortable sofa and elegant armchairs around a richly patterned rug. A brick fireplace adds warmth, while a television is positioned in front of the seating area. Natural light fills the space from large windows.
Flat in Westport
4.91 out of 5 average rating, 290 reviews

Spacious Westport Apt surrounded by nature!

Spacious mother-in-law basement apartment with private entrance that opens to the backyard. Large windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space for up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, hikes, wonderful bakeries and restaurants.

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, 69 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, 141 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, 376 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.

Guest favourite
The exterior of a charming turn-of-the-century farmhouse is displayed, featuring a white facade and a welcoming porch. A red barn is positioned to the right, set against a backdrop of lush green lawn and trees under a clear blue sky.
Flat in Milford
4.87 out of 5 average rating, 296 reviews

The Farmhouse Estate Apartment

Perfect for families & groups! This 3 bed & 1 bath unit is located on the 1st floor of a turn-of-the-century Farmhouse outfitted with modern amenities. The unit has been specifically designed for Airbnb use and has a boutique hotel feel. Enjoy hardwood floors, Queen memory foam mattresses, high ceilings, keypad door lock (no keys needed), central air, private deck & beautiful views of a 1 acre yard with adjacent apple orchard. No parties or events allowed.

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, 164 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
4.95 out of 5 average rating, 199 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

When is the best time to visit Bridgeport?

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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 $26 SGD 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