Vacation rentals in Bridgeport

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Top-rated vacation rentals in Bridgeport

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

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Top guest favorite
A spacious bedroom features a queen-sized bed with a light-colored quilt. Two elegant armchairs are positioned around a glass-topped table. Natural light floods in through multiple windows adorned with lace curtains, providing views of the verdant surroundings.
Guest suite in Fairfield
4.93 out of 5 average rating, 182 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; exclusive use of kitchen (was the main kitchen of the house); private entrance to space thru side door of the house. Two large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Guest favorite
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, 102 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 favorite
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, 189 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 favorite
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.
Apartment in Milford
4.97 out of 5 average rating, 623 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!

Guest favorite
An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.
Home in Milford
4.97 out of 5 average rating, 258 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Top guest favorite
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, 168 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
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
4.91 out of 5 average rating, 147 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 favorite
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, 386 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.

Superhost
Home in Bridgeport
4.9 out of 5 average rating, 78 reviews

Lavish retreat near downtown

Kick back and relax in this home away from home. Motion sensored lights with spacious waterfall shower unit and outdoor space for dinning and lounge. Full kitchen with multiple tv units(Netflix, Hbo,Hulu, paramount & Starz) and rest areas. Coffee and tea available. 5 mins away from downtown , accessible to trains & bus. Parking available in backyard of property . (Ceiling are low(6’2) due to the space being downstairs ) ( 1 Queen bed, 1 Sofa bed)

Top guest favorite
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.
Apartment in Fairfield
4.98 out of 5 average rating, 172 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.

Top guest favorite
Home in Fairfield
4.96 out of 5 average rating, 202 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.

Superhost
A corner of the apartment features unique hand-tinted windows that create colorful reflections. A cozy armchair sits beside a fireplace, surrounded by potted plants. The space is complemented by a woven area rug and a light-colored bed with a simple texture.
Apartment in Bridgeport
4.89 out of 5 average rating, 146 reviews

Stylish Sheek Loft Ricport Studio 2, Downtown

Please note location and area before booking!!! (DONT BOOK if you don’t know it’s loud and busy) Conveniently located Downtown in the city of Bridgeport. Feel free to light a fire🔥. Unique hand tinted windows provides the space with an open feel although it is a small space. Queen size bed, fireplace, and aesthetics sets this apartment apart from any rental you can find. *pet fee for pets. Please let me know in advance.

Popular amenities for Bridgeport places to stay

When is the best time to visit Bridgeport?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,758 GYDG$20,712 GYDG$21,549 GYDG$20,922 GYDG$25,315 GYDG$24,897 GYDG$24,478 GYDG$25,106 GYDG$23,641 GYDG$22,804 GYDG$23,014 GYDG$23,014 GYD
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Frequently Asked Questions

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

    Experience the best of Bridgeport with our townhouse rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

    Yes! Work meets play with ease at over 190 vacation 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 410 vacation rentals in Seaside Park, over 480 vacation rentals in Steel Point, and over 410 vacation rentals in Black Rock.

  • Are there family-friendly vacation rentals in Bridgeport?

    Bridgeport has more than 140 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Bridgeport?

    Four-legged friends are welcome in Bridgeport. Choose from more than 80 vacation rentals for guests traveling with pets.

  • Are there Bridgeport house rentals on Airbnb with pools?

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

  • Do townhouse rentals in Bridgeport have air conditioning?

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

  • Do apartment rentals in Bridgeport have wifi?

    Absolutely! We offer over 100 apartment rentals with wifi in Bridgeport. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Bridgeport have a bbq area?

    Absolutely! We offer over 10 apartment 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 vacation rentals in Bridgeport

  • Total vacation rentals

    Explore 320 vacation rentals in Bridgeport

  • Nightly prices starting at

    Bridgeport vacation rentals start at G$4,184 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,930 verified reviews to help you choose

  • Family-friendly vacation rentals

    140 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

  • Wi-Fi availability

    310 of Bridgeport vacation rentals include wi-fi 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