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Holiday houses in Bridgeport

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Top-rated holiday rentals in Bridgeport

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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, 248 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.

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, 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.

Top Guest favourite
Apartment in Fairfield
5 out of 5 average rating, 74 reviews

Modern Studio Near Fairfield & Sacred Heart Univ

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!

Guest favourite
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, 259 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!

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
4.94 out of 5 average rating, 77 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.

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, 171 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, 148 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, 387 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
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman
4.96 out of 5 average rating, 435 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Superhost
The kitchen features white cabinetry with gold hardware and a black tile backsplash. A marble countertop holds a sink and a stove, while a microwave and various supplies are arranged above. Ample storage is provided, enhancing the functional design of the space.
Home in Bridgeport
4.9 out of 5 average rating, 80 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 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.
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 favourite
Home in Stratford
5 out of 5 average rating, 32 reviews

Bright, Stylish & Cozy Suite

Welcome to your calm and peaceful retreat — a bright, stylish, and cozy suite designed for comfort and relaxation. Enjoy a sunny bedroom filled with natural light and beautiful views that make every morning special. This private space offers a quiet escape from the city buzz, blending modern style with a warm, homey feel. Perfect for those who appreciate calm surroundings, soft sunlight, and a touch of elegance in every corner.

Popular amenities for Bridgeport holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Bridgeport's top sights

Seaside Park

52 locals recommend

Beardsley Zoo

110 locals recommend

University of Bridgeport

18 locals recommend

Fairfield University

20 locals recommend

Jennings Beach

54 locals recommend

Two Roads Brewing Co

40 locals recommend

Other great holiday rentals in Bridgeport

Apartment in South End
4.52 out of 5 average rating, 88 reviews

Historic Brownstone Close to Beach & Amphitheater

Guest favourite
Home in Bridgeport
4.79 out of 5 average rating, 187 reviews

Golden Colonial Home

A modern kitchen features sleek cabinetry, a marble backsplash, and stainless steel appliances. A spacious countertop provides seating for two at stylish, high-backed stools. Natural light illuminates the area, highlighting decorative kitchen items and the open layout that enhances the space.
Apartment in Bridgeport
4.78 out of 5 average rating, 36 reviews

Retro Bridgeport Apartment

Superhost
The exterior of the Courtyard by Marriott Shelton is showcased, featuring a modern, multi-story structure with large windows. The entrance is prominent, framed by landscaped greenery and a spacious parking area. The building is complemented by soft evening lighting.
Hotel room in Shelton
4.81 out of 5 average rating, 154 reviews

Close to Yale University + The Bistro. Pool. Gym.

A rustic cabin with green log siding is surrounded by tall trees. The front porch features two black chairs, and a storage trunk adds a practical touch. A decorative star and wall clock enhance the inviting exterior, while a garden area complements the natural setting.
Bungalow in Trumbull
4.83 out of 5 average rating, 254 reviews

Cozy, romantic cabin by the lake.

A welcoming living area features two comfortable sofas and a plush ottoman, set on a patterned area rug. Warm wooden accents are highlighted by natural light from large windows. Sliding barn doors provide access to an adjacent space, with a cozy reading nook visible in the background.
Home in Bridgeport
4.8 out of 5 average rating, 45 reviews

Quintessential Cozy Haven, Brooklawn Beauty

Superhost
A spacious lower-level room features a large bed, a sofa bed, and a dining area with a table and chairs. The brick accent wall adds character, while the tiled floor complements the functional layout. A work desk with a desktop computer is also present.
Private room in Stratford
4.88 out of 5 average rating, 177 reviews

Business or Weekend escape*

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.
Apartment in South End
4.89 out of 5 average rating, 123 reviews

Seaside Studio in Historic Bridgeport Brownstone

When is the best time to visit Bridgeport?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$193 NZD$193 NZD$193 NZD$169 NZD$205 NZD$202 NZD$198 NZD$203 NZD$191 NZD$185 NZD$186 NZD$186 NZD
Avg. temp0°C1°C4°C10°C16°C21°C24°C24°C20°C14°C8°C3°C

Frequently Asked Questions

  • What are the best places to stay in Bridgeport?

    Stays in Black Rock, Downtown, and areas near Seaside Park are often suggested for their lively atmosphere and proximity to local dining and waterfront activities. These neighborhoods provide easy access to arts spaces and parks.

  • What are the best things to do in Bridgeport with kids?

    Kids can explore animal exhibits at Beardsley Zoo, run and play at Seaside Park, or enjoy hands-on learning in local museums. Waterfront playgrounds and seasonal events often draw families throughout the year.

  • What are some of the best things to do in Bridgeport?

    Bridgeport has lively arts spaces, waterfront parks such as Seaside Park, and family-friendly attractions like the Beardsley Zoo. Many visitors enjoy shopping at local markets and attending cultural or seasonal festivals.

  • How is the weather in Bridgeport?

    Bridgeport has cold winters near 24–44°F (-4–7°C), and warm, humid summers averaging 67–83°F (19–29°C) with occasional rainfall. Spring and autumn are milder, with comfortable temperatures and changing foliage.

  • When is the best time to visit Bridgeport?

    Late spring through early autumn is often recommended for visitors who prefer milder temperatures and outdoor events. Winter brings colder weather and indoor arts activities, while autumn features colorful foliage and community festivals.

  • What are the best places to visit in Bridgeport?

    Bridgeport has family-friendly attractions like the Beardsley Zoo, waterfront parks, and museums highlighting local history. Many visitors enjoy the creative atmosphere at art galleries, and quiet moments in green spaces around the city.

  • What are some hiking trails in Bridgeport?

    Bridgeport has walking and nature trails in places like Beardsley Park and Seaside Park, with views of woodlands and waterfront areas. Nearby nature preserves offer additional paths for birdwatching and exploring the outdoors.

  • What are some family activities we can do in Bridgeport?

    Families can explore Beardsley Zoo, enjoy picnic spots and playgrounds in Seaside Park, or discover hands-on exhibits at local museums. Seasonal festivals, outdoor concerts, and waterfront activities are also frequently suggested.

  • What are some of the best day trip ideas from Bridgeport?

    Many visitors explore quieter beaches near Long Island Sound, art galleries and shops in nearby towns, or forested hikes in regional parks surrounding Bridgeport. Seasonal activities, local farms, and outdoor trails are frequently suggested.

  • Are there any pet friendly accommodations available in Bridgeport?

    Many vacation rentals in Bridgeport are pet friendly, allowing visitors to stay with dogs or cats. Neighborhoods such as Black Rock and Downtown frequently have welcoming spaces near parks and walking areas.

  • What are some local tips for visiting Bridgeport?

    Locals often suggest exploring the waterfront early in the morning for a quieter experience, and attending neighborhood markets or festivals to sample diverse foods. Public transit and walking are convenient for moving between popular attractions and parks.

  • What is Bridgeport known for?

    Bridgeport is known for its historic waterfront, diverse arts and music communities, and Connecticut’s only zoo. The city also has locally rooted culinary traditions and a strong history in manufacturing and innovation.

  • What are the best hidden gems to explore in Bridgeport?

    Bridgeport has smaller galleries, murals by local artists, and community theaters that highlight creative voices in the city. Waterfront trails in less crowded parks, and neighborhood bakeries featuring Portuguese and Brazilian treats, are often favorite discoveries.

  • What are the best foods to try in Bridgeport?

    Bridgeport’s food scene features locally rooted favorites such as New England–style pizza, fresh seafood, and Portuguese baked goods. Many visitors enjoy exploring casual restaurants and bakeries around the Black Rock neighborhood.

  • What should I bring for a trip to Bridgeport?

    Pack comfortable walking shoes, weather-appropriate clothing, and a light waterproof jacket. If visiting in summer, sunscreen and water bottles are helpful for outdoor activities; in winter, a warm coat and gloves are suggested.

  • What is the nightlife in Bridgeport like?

    Bridgeport has a mix of laid-back bars, music venues, and performance spaces, especially around Downtown and the Harbor area. The scene features live music, occasional comedy nights, and locally inspired cocktails.

  • What are the most popular events or festivals in Bridgeport?

    Bridgeport has lively arts, music, and cultural festivals, often focused around areas such as Downtown and the waterfront. Events like outdoor concerts at Seaside Park are frequently suggested, highlighting local traditions and a wide mix of performances.

  • Are there family friendly vacation rentals in Bridgeport?

    Bridgeport has a variety of family-friendly vacation rentals throughout areas like Black Rock, Seaside, and Downtown. These neighborhoods typically have easy access to parks, playgrounds, and local attractions.

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 $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 7,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    140 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 80 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

  • Wi-Fi availability

    310 of Bridgeport holiday 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

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