Compare Vacation Rentals & Airbnb in Bridgeport, CT

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Bridgeport, CT vacation rentals
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393 Rentals and Airbnb in Bridgeport, CT

Best family friendly Bridgeport, CT vacation rentals

Among the 393 accommodations in Bridgeport, CT, here are the 4 best family friendly rentals

Remodeled Cozy Country Cape - Bridgeport, CT
10 40 reviews

Remodeled Cozy Country Cape

apartment, Fairfield
This Fairfield apartment is conveniently located just a short distance from the town's attractions and amenities, making it an ideal base for exploring the area. The property has received excellent ratings for its cleanliness, location, and overall experience.
The spacious apartment can comfortably accommodate up to four guests and features a modern and stylish open plan layout. Guests can enjoy a fully equipped kitchen, a private garden, and a comfortable living area with a TV, perfect for relaxing after a day of sightseeing.
Stay At Black Rock Harbor - Bridgeport, CT
9.9 70 reviews

Stay At Black Rock Harbor

apartment, Bridgeport
This apartment is in Black Rock, a short walk from the beach and downtown, making it ideal for exploring the area. It has excellent user, location and cleanliness ratings, ensuring a comfortable stay.
This home has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It has a fully equipped kitchen, a backyard with a picnic table, a Tesla EV charger, and offers flexible check-in and hassle-free departure.
Modern Beach Bungalow - Bridgeport, CT
9.9 78 reviews

Modern Beach Bungalow

apartment, Fairfield
This modern house in Fairfield is just a short walk from the beach, offering easy access to the sand and the serene Long Island Sound. The accommodation has received excellent ratings for its location, cleanliness, and overall experience.
The house features a spacious open plan layout, comfortably accommodating up to four guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a private garden, and a large smart TV. Guests can also enjoy the outdoor shower, beach amenities, and convenient access to nearby golf courses, hiking trails, and the town's shops and restaurants.
Downtown Fairfield 3 Bedroom Colonial - Bridgeport, CT
9.9 140 reviews

Downtown Fairfield 3 Bedroom Colonial

apartment, Fairfield
This charming three-bedroom Colonial house is situated on a peaceful street in Fairfield, just 0.6 kilometres from the lively Post Road and 1.1 kilometres from the Fairfield Train Station. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house is spacious and can comfortably accommodate up to six guests. Guests can enjoy a range of amenities including a fully equipped kitchen, a garden, a basketball court, and air conditioning.

Best Bridgeport, CT vacation rentals with a pool

Among the 393 accommodations in Bridgeport, CT, here are the 4 best rentals with a pool

*Pool Open* Multi Family Retreat - Nature Spa Fire - Bridgeport, CT
9.7 7 reviews

*Pool Open* Multi Family Retreat - Nature Spa Fire

farm, Fairfield
This Fairfield County farmhouse, located within walking distance of Fairfield's beaches, restaurants, and shops, offers convenient access to New York City via a 45-minute train journey from Grand Central Terminal or a 1-hour drive (approx. 64km).
The property comprises two homes with designer interiors, sleeping up to 14 guests across 6 bedrooms and 4 bathrooms, boasting a swimming pool, jacuzzi, large garden, and chef's kitchen; amenities include a dishwasher, microwave, and large TVs.
Summer Beach Escape - Bridgeport, CT
10 2 reviews

Summer Beach Escape

apartment, Fairfield
This newly renovated residence is located on a quiet cul-de-sac in Fairfield's prime beach district, just 200 meters from the beach, town centre, and train station.
This four-bedroom, five-bathroom apartment comfortably accommodates eight guests and features a heated gunite pool, outdoor kitchen, and resort-style setting for a luxurious stay.
Business Or Weekend Escape - Bridgeport, CT
9.2 58 reviews

Business Or Weekend Escape

apartment, Stratford
This Stratford holiday home is situated within 3.2 kilometres of the Housatonic River, Perry House, and the Stratford Historical Society's Captain David Judson House, offering easy access to Stratford's historical landmarks.
The one-bedroom property sleeps four guests, boasting a sofa bed, Smart TV, barbecue facilities, and is within easy reach of Academy Hill and Newfield Park, perfect for outdoor recreation.
Cozy Studio Unit - Bridgeport, CT
9.9 80 reviews

Cozy Studio Unit

apartment, Trumbull
This Trumbull studio apartment is conveniently located within a 6.4km radius of Bridgeport Hospital, Sacred Heart University, and the Trumbull Mall, offering easy access to major highways and the coast.
The self-contained unit sleeps four, features a kitchenette with fridge, freezer and microwave, plus a private backyard with gazebo, swimming pool and on-site parking; nearby attractions include the seaside beach (8km) and Yale University (14.5km).

Frequently Asked Questions about vacation rentals in Bridgeport, CT

  • Which neighborhood in Bridgeport, CT should you consider for a vacation rental?

    The Black Rock neighbourhood is a great option for a vacation rental. It's a charming area with a mix of residential streets and shops, and it's close to the beach. The Southport neighbourhood is another good choice, it's a bit more upscale and has a beautiful waterfront.
  • What are the best Airbnb and vacation rentals in Bridgeport, CT?

  • What are the top family-friendly attractions in Bridgeport, CT?

    The Beardsley Zoo is a popular choice for families, as is the Discovery Museum and Planetarium. If you're looking for something a little different, the Stepping Stones Museum for Children is a great option. The beach is also a great place to spend a day with the family, and there are a number of parks and playgrounds in the city.
  • What are the most popular Airbnbs in Bridgeport, CT?

  • When is the best time to book a vacation rental in Bridgeport, CT?

    The best time to book a vacation rental in Bridgeport is during the shoulder season, from April to May or September to October. You'll get better deals on rentals and the weather is still pleasant. Summer is also a popular time to visit, but prices tend to be higher.
  • What are the best vacation rentals with a pool in Bridgeport, CT?

    Victorian Apartment, 2-story Historic Carriage House On Estate and Come And Stay At Cozy Home are the best vacation rentals with a pool in Bridgeport, CT.

  • What events or festivals should visitors check out in and around Bridgeport, CT?

    The Bridgeport Summerfest is a big event that takes place in July, and there are plenty of other festivals and events throughout the year. Check out the calendar of events on the city's website for more information.
  • What are the best rentals for families and kids in Bridgeport, CT?

    The best rentals for families and kids in Bridgeport, CT are The Classic Getaway 2br Fairfield & Seaside Beach, Polita’s Place #1 and Lovely 2bdrm In Cozy Neighborhood.

  • What are the best budget-friendly activities in Bridgeport, CT?

    The city has a number of free or low-cost activities, including walking the boardwalk, visiting the Beardsley Zoo, and exploring the various parks and gardens. You can also find a number of budget-friendly restaurants and cafes throughout the city.
  • What are the best rentals or Airbnbs with a jacuzzi in Bridgeport, CT?

    The best vacation rentals or Airbnb with a jacuzzi in Bridgeport, CT are Vrbo Property, Black Rock Home and 250 M² Casa ∙ 4 Camere Da Letto ∙ 9 Ospiti.

  • What are the best restaurants with local dishes in Bridgeport, CT?

    There are a number of great restaurants in Bridgeport, but some of the best for local dishes are The Lobster House and The Black Duck. Both serve up fresh seafood, and The Black Duck also has a great selection of local craft beers.
  • What are the best walking or cycling routes in Bridgeport, CT?

    The Seaside Park is a great place for a walk or bike ride, and there are also a number of trails in the city's parks. If you're looking for a longer ride, the Pequonnock River Trail is a great option, it follows the river for over 10 km.
  • Are there pet-friendly attractions in Bridgeport, CT?

    Yes, there are a number of pet-friendly attractions in Bridgeport, including the Beardsley Zoo, the Seaside Park, and a number of restaurants and cafes. Be sure to check with the individual businesses to confirm their pet policies.
  • What are the benefits of choosing a vacation rental in Bridgeport, CT?

    Vacation rentals offer a number of benefits over hotels, including more space, privacy, and the ability to cook your own meals. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Bridgeport, CT?

    Bridgeport is home to the Bridgeport Sound Tigers, a minor league hockey team. There are also a number of other sports facilities in the city, including the Webster Bank Arena, which hosts a variety of events, including concerts and sporting events.

Popular destinations

Best Bridgeport, CT vacation rentals with a balcony

Cozy Condo With Yard And Patio. Long-stay Discount Available - Bridgeport, CT
No reviews

Cozy Condo With Yard And Patio. Long-stay Discount Available

apartment, Fairfield
Apartment listing. This accommodation is located in Fairfield.
Facilities and services include a terrace, a dish washer and a kitchen. Take advantage of the Free Parking with this accommodation.
Stareway To Heaven Su - Bridgeport, CT
10 22 reviews

Stareway To Heaven Su

apartment, Fairfield
This Fairfield beachfront flat, situated a short walk from Fairfield's shops and restaurants, offers easy access to Bridgeport and Westport.
The five-bedroom, four-bathroom property sleeps eight, boasting a chef's kitchen, rooftop deck with coastal views, and optional beach cruiser and paddleboard rentals.
Landing | Chic 1bd In Steelpointe Harbor - Bridgeport, CT
No reviews

Landing | Chic 1bd In Steelpointe Harbor

apartment, Bridgeport
This premium apartment, located in The August at Steelpointe Harbor in Bridgeport, CT, offers expansive floor-to-ceiling windows with harbour views and is situated within 5 kilometres of Silver Sands State Park and The Coastal Centre at Milford Point, with easy access to Beardsley Zoo and The Discovery Museum.
This 62 square metre flat, accommodating up to two guests, features an open-concept kitchen with quartz countertops, air conditioning, and a private terrace, whilst being conveniently positioned near the Hartford HealthCare Amphitheater and Total Mortgage Arena, with pet-friendly options available.
The B&w Haven: Stylish 3br Escape With Private Office By Li Ferry - Bridgeport, CT
No reviews

The B&w Haven: Stylish 3br Escape With Private Office By Li Ferry

apartment, Bridgeport
This Bridgeport apartment, situated in the Brooklawn-St. Vincent neighbourhood, offers convenient proximity to Beardsley Zoo, the Discovery Museum, and Fairchild Wheeler Golf Course.
The 186 square metre (1991 square feet) property comprises four bedrooms, one bathroom, and accommodates six guests, boasting a stylish black and white interior, a fully equipped kitchen, high-speed internet, smart TVs, and a private balcony with access to a shared garden and parking.

Best Bridgeport, CT vacation rentals with parking

Lovely 5 Bedroom Beach House With Large Backyard - Bridgeport, CT
10 10 reviews

Lovely 5 Bedroom Beach House With Large Backyard

apartment, Fairfield
This Fairfield house is situated just a short walk from the beach, the town centre, and the Metro North train station, making it a convenient base for exploring the area. The surrounding neighbourhood is quiet and residential, offering a peaceful retreat from the hustle and bustle of city life.
The house has 5 bedrooms and 3 bathrooms, providing ample space for up to 9 guests. It features a fully equipped kitchen, a spacious living room with a fireplace, a large garden with a patio, and parking for multiple vehicles.
The B&w Haven 3br Private Office By Li Ferry - Bridgeport, CT
8.7 3 reviews

The B&w Haven 3br Private Office By Li Ferry

apartment, Bridgeport
This Bridgeport apartment, situated 13km from Silver Sands State Park and 18km from the Connecticut Post Mall, offers easy access to both coastal and shopping attractions.
The 186 square metre, three-bedroom property sleeps eleven guests and boasts a fully equipped kitchen, free Wi-Fi, on-site parking, a shared garden, and a fireplace; additional cleaning is available fortnightly.
3br Family Apt, Renovated With Easy Check-in - Bridgeport, CT
9.4 54 reviews

3br Family Apt, Renovated With Easy Check-in

apartment, Bridgeport
This apartment is conveniently located just a short distance from Seaside Park and Captain's Cove Seaport, offering easy access to the beach and Bridgeport's waterfront attractions. It has consistently received excellent ratings for cleanliness, location, and overall user experience.
The apartment has three bedrooms, accommodating up to eight guests, perfect for families or groups of friends. The fully equipped kitchen, comfortable living area, and smart TVs provide everything you need for a relaxing and enjoyable stay, while the dedicated workspace with Wi-Fi is ideal for those who need to work remotely.
Spacious Cottage Loft - Bridgeport, CT
10 111 reviews

Spacious Cottage Loft

apartment, Bridgeport
The Spacious Cottage Loft is located in Black Rock, a charming seaside neighbourhood in Bridgeport, Connecticut, set on the grounds of a historic Victorian house dating back to the 1840s. The cottage has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The cottage has one bedroom and one bathroom, comfortably accommodating two guests. It offers a range of amenities including a fully equipped kitchen, two smart TVs, a dedicated workspace, a private patio, and access to a swimming pool during the warmer months.
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