Compare Vacation Rentals & Airbnb in Bridgeport, CT

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

Luxurious, Direct Waterfront Home With Private Beach - Bridgeport, CT
10 18 reviews
Bridgeport, CT
23/12 – 06/01
$2058/nighttotal: $28812 (14 )

Luxurious, Direct Waterfront Home With Private Beach

4 10
apartment, Milford
This Milford beachfront property offers unparalleled ocean views, being less than 1.6km from Walnut Beach and Silver Sands, and within 4.8km of Port Milford and The Coastal Centre at Milford Point.
This luxurious 418 square metre house boasts four bedrooms, four bathrooms, sleeps ten guests, and includes a modern kitchen, jacuzzi, fitness centre, private balcony, and direct beach access, plus free Wi-Fi.
Stylish Sheek Loft 
Ricport Studio 2, Downtown - Bridgeport, CT
9.8 148 reviews
Bridgeport, CT
01/08 – 03/08
$208/nighttotal: $416 (2 )

Stylish Sheek Loft Ricport Studio 2, Downtown

1 2
apartment, Bridgeport
This Bridgeport studio apartment is centrally located in downtown Bridgeport, offering easy access to numerous restaurants and bars.
The pet-friendly unit, sleeping up to two guests, features a queen-size bed, a kitchenette with a fridge and microwave, air conditioning, and a unique hand-tinted window.
Cozy Private 2br/2ba Retreat W/separate Entrance - Bridgeport, CT
10 1 review
Bridgeport, CT
23/12 – 06/01
$348/nighttotal: $4872 (14 )

Cozy Private 2br/2ba Retreat W/separate Entrance

1 4
apartment, Bridgeport
This newly renovated two-bedroom flat in Bridgeport is located in a residential area, offering a private and peaceful stay with convenient access to local amenities.
This basement apartment accommodates up to four guests and features a fully equipped kitchen, two bathrooms, a bar area, and in-unit laundry, with assigned parking and air conditioning for year-round comfort.
Quaint Private Two Bdrm With Balcony, Stream View! - Bridgeport, CT
8.9 9 reviews
Bridgeport, CT
23/12 – 06/01
$309/nighttotal: $4326 (14 )

Quaint Private Two Bdrm With Balcony, Stream View!

1 4
apartment, Bridgeport
This two-bedroom flat in Bridgeport offers convenient access, being just a 4-minute drive from Sacred Heart University.
This Airbnb provides high-speed WiFi, a fully equipped kitchen, and a private balcony, comfortably accommodating up to five guests with new Serta Sleeper mattresses.
Polita’s Place #1 - Bridgeport, CT
9.9 98 reviews
Bridgeport, CT
23/12 – 06/01
$375/nighttotal: $5250 (14 )

Polita’s Place #1

1 4
apartment, Bridgeport
This three-bedroom flat is conveniently located in the centre of Bridgeport, within walking distance of the Beardsley Zoo and a short drive from the Downtown Bridgeport area and the Bridgeport Art Center. It has received excellent ratings for location, cleanliness and user experience.
The flat is spacious and has a modern and coastal decor. It comes with a fully equipped kitchen, air conditioning, a garden, parking and internet access, making it perfect for a comfortable and enjoyable stay.
The B&w Haven 5br Home With Yard Theater + Office - Bridgeport, CT
8.8 9 reviews
Bridgeport, CT
23/12 – 06/01
$764/nighttotal: $10696 (14 )

The B&w Haven 5br Home With Yard Theater + Office

5 10
apartment, Bridgeport
This five-bedroom house in Bridgeport's Brooklawn-St. Vincent neighbourhood is a short walk from the Bridgeport Downtown South Historic District and St Vincent's Medical Center, with Svihra and Lafayette Parks less than 1.6km away.
This 186 square metre family home, sleeping up to 11 guests, boasts a fully equipped kitchen, free WiFi, a balcony, and parking, plus housekeeping is available on request; Bridgeport Station is approximately 2.4km away.
Comfy And Convenient: A Home Away From Home - Bridgeport, CT
10 2 reviews
Bridgeport, CT
27/06 – 04/07
$355/nighttotal: $2485 (7 )

Comfy And Convenient: A Home Away From Home

1 1
apartment, Bridgeport
This Bridgeport studio apartment is conveniently located near the Metro-North train station, a three-minute (4.8km) drive away, offering easy access to New York and Boston and proximity to local restaurants and supermarkets.
The self-contained unit features a fully equipped kitchenette, a private bathroom with a shower and bath, and accommodates one guest; a private entrance ensures privacy despite being on the property owner's premises.
Modern Studio Near Fairfield & Sacred Heart Univ - Bridgeport, CT
10 81 reviews
Bridgeport, CT
01/08 – 03/08
$222/nighttotal: $444 (2 )

Modern Studio Near Fairfield & Sacred Heart Univ

1 2
studio, Fairfield
This Fairfield studio apartment is conveniently located near Fairfield University and Sacred Heart University, offering easy access to shops and beaches, and is within easy reach of New York City via public transport.
The self-contained unit features a queen-size bed, 70” Samsung Smart TV, in-suite laundry, a modern kitchen, and parking, accommodating up to three guests.
2 Bed Apt In Blackrock By Beach - Bridgeport, CT
9.0 1 review
Bridgeport, CT
29/07 – 07/08
$434/nighttotal: $3906 (9 )

2 Bed Apt In Blackrock By Beach

2 2
apartment, Bridgeport
This two-bedroom flat in Bridgeport's Black Rock neighbourhood is conveniently located near the beach, approximately 16 km from Silver Sands State Park and 22 km from the Connecticut Post Mall.
The 1000 square metre property boasts a fully equipped kitchen, air conditioning, Wi-Fi, and accommodates up to six guests, making it ideal for families or groups visiting Bridgeport.
Lake House Cozy To Relax With A Family. 6 Bedroom Very Spacious House. - Bridgeport, CT
9.6 5 reviews
Bridgeport, CT
23/12 – 06/01
$3670/nighttotal: $51380 (14 )

Lake House Cozy To Relax With A Family. 6 Bedroom Very Spacious House.

6 10
apartment, Trumbull
This Trumbull, Connecticut holiday home is conveniently located near major highways, offering easy access to local parks such as Boothe Memorial Park and museums including the National Helicopter Museum.
The six-bedroom, four-bathroom property sleeps twelve guests and boasts amenities including a jacuzzi, garden, free WiFi, and a fully equipped kitchen with dishwasher; nearby attractions include Beardsley Zoo and the Discovery Museum.
Charming 2-bedroom Apartment In Delightful Bridgeport With Wifi - Bridgeport, CT
Bridgeport, CT
28/08 – 18/12
$190/nighttotal: $21280 (112 )

Charming 2-bedroom Apartment In Delightful Bridgeport With Wifi

2 1
apartment, Bridgeport
This Bridgeport apartment, situated in the Brooklawn-St. Vincent neighbourhood, is an 11-minute walk (approximately 0.8 km) from Svihra Park and a 2-minute drive (approximately 0.3 km) from Bridgeport's Downtown South Historic District.
The two-bedroom, one-bathroom flat offers on-site parking, a fully equipped kitchen, and sleeps up to two guests, with amenities including towels, bedding and heating; nearby attractions include the Bridgeport Bluefish Baseball Club and Hartford HealthCare Amphitheater.
Walk To Beach, Seaside Park, University - Bridgeport, CT
9.5 81 reviews
Bridgeport, CT
27/06 – 04/07
$247/nighttotal: $1729 (7 )

Walk To Beach, Seaside Park, University

1 2
apartment, Bridgeport
This one-bedroom flat is situated just a short walk from the University of Bridgeport and Seaside Park, offering easy access to both the beach and the city centre. Guests have consistently rated this property as excellent for its location, cleanliness and overall experience.
The flat is ideal for couples, with a comfortable double bed and a fully equipped kitchen. Amenities include a large smart TV, air conditioning, free parking and stunning views of Long Island Sound.

Best family friendly Bridgeport, CT vacation rentals

Among the 276 accommodations in Bridgeport, CT, here are the 4 best family friendly rentals

Renovated Cape Near Beach With Fire Pit - Bridgeport, CT
Bridgeport, CT
01/08 – 03/08
$978/nighttotal: $1956 (2 )

Renovated Cape Near Beach With Fire Pit

3 2
house, Fairfield
Fairfield Retreat, a one-bedroom house in Fairfield, Connecticut, is conveniently located 18km from the Connecticut Post Mall, 18km from Silver Sands State Park, and 35km from Yale University.
This self-catering property sleeps up to 17 guests and boasts two bathrooms, free Wi-Fi, private parking, a garden, and air conditioning.
Remodeled Cozy Country Cape - Bridgeport, CT
9.9 34 reviews
Bridgeport, CT
23/12 – 06/01
$722/nighttotal: $10108 (14 )

Remodeled Cozy Country Cape

1 4
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.
Beechmont-charming Colonial For Events And Getaways! - Bridgeport, CT
8.0 1 review
Bridgeport, CT
13/11 – 15/11
$2305/nighttotal: $4610 (2 )

Beechmont-charming Colonial For Events And Getaways!

6 10
house, Bridgeport
This Bridgeport property, a colonial-style house, is located 13.7km from Silver Sands State Park and 19.3km from the Connecticut Post Mall, offering convenient access to local attractions.
The 307 square metre dwelling boasts one bedroom, four bathrooms, and accommodates up to 23 guests, featuring a fully equipped kitchen, free Wi-Fi, private parking, and a terrace/garden.
Bright, Private 1,000 Sq. Ft. 1-bedroom Apartment - Bridgeport, CT
10 83 reviews
Bridgeport, CT
29/07 – 07/08
$222/nighttotal: $1998 (9 )

Bright, Private 1,000 Sq. Ft. 1-bedroom Apartment

1 2
apartment, Fairfield
This Fairfield apartment is located just a short distance from the Fairfield Town Open Space and a creek, offering a peaceful setting with views of nature. It has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This self-catering property is a second-story suite with a separate entrance, accommodating up to three guests. The apartment features a well-equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as a comfortable living area with a large screen TV, a selection of board games, books, and movies, and a modern bathroom.

Best Bridgeport, CT vacation rentals with a pool

Among the 276 accommodations in Bridgeport, CT, here are the 4 best rentals with a pool

Fairfield Favorite - Bridgeport, CT
10 18 reviews
Bridgeport, CT
23/12 – 06/01
$2230/nighttotal: $31220 (14 )

Fairfield Favorite

1 4
apartment, Fairfield
This Fairfield property is situated on a hill overlooking Brooklawn Country Club, offering a peaceful escape from the city bustle just 1.5 km from the centre of Fairfield. The accommodation is set in a quiet and tranquil setting, ideal for a relaxing getaway.
The house is a spacious four-bedroom property, comfortably accommodating up to eight guests. It boasts a modern kitchen, a swimming pool, a sauna, and a fitness centre, ensuring a comfortable and enjoyable stay.
The House Haven - Bridgeport, CT
10 1 review
Bridgeport, CT
27/06 – 04/07
$695/nighttotal: $4865 (7 )

The House Haven

4 2
apartment, Stratford
The House Haven is situated in Stratford, Connecticut, just a short distance from the town's beaches and historic district. It has received excellent ratings for cleanliness and location, with guests describing it as a very good place to stay.
The property offers four bedrooms and one bathroom, comfortably accommodating up to six guests. It features a range of amenities, including a swimming pool, Jacuzzi, fitness centre, and a spacious garden with a playground, making it ideal for families.
Lovely Home By The Beach In Coveted Lordship - Bridgeport, CT
10 6 reviews
Bridgeport, CT
23/12 – 06/01
$972/nighttotal: $13608 (14 )

Lovely Home By The Beach In Coveted Lordship

1 4
apartment, Stratford
This Lordship, Connecticut holiday home is a two-minute walk from the beach, five minutes from waterfront restaurants, and ten minutes (approximately 1.6km) from Stratford train station and the Port Jefferson ferry.
The three-bedroom, one-bathroom property sleeps six, boasting a heated saltwater pool, private golf cart, and access to paddleboards, beach equipment, and nearby amenities including a nine-hole golf course and various sports courts.
6-bedroom House With Fitness Room And Pool In Westport - Bridgeport, CT
Bridgeport, CT
23/12 – 06/01
$3533/nighttotal: $49462 (14 )

6-bedroom House With Fitness Room And Pool In Westport

7 10
apartment, Westport
This spacious 604 square metre residence in Westport offers 7 bedrooms and 8 bathrooms, accommodating up to 14 guests with a private swimming pool, outdoor pavilion with a fireplace, and an on-site fitness room.
Conveniently located near the Country Club of Fairfield and Gateway Shopping Centre, this property provides easy access to golf courses, shopping, and entertainment at the Pitt Centre and Total Mortgage Arena, with pets and families welcome.

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.

Destinations nearby

Best Bridgeport, CT vacation rentals with a balcony

Cozy Cottage With Fire Pit, Near Beach, 1 Mile To Nyc Train - Bridgeport, CT
10 36 reviews
Bridgeport, CT
01/08 – 03/08
$1286/nighttotal: $2572 (2 )

Cozy Cottage With Fire Pit, Near Beach, 1 Mile To Nyc Train

3 2
apartment, Fairfield
This Fairfield property is situated within 5km of Fairfield University, the Bellarmine Museum of Art, Longfellow Park, Bridgeport's Downtown South Historic District, and Seaside Park, and an 18-minute walk from Fairfield Metro station.
This four-bedroom, two-bathroom house sleeps eight guests and boasts a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a garden, parking, Wi-Fi, and an on-site games room; pets are welcome.
Renovated Cape Near Beach, With Fire Pit And Bbq, 1 Mile To Nyc Train - Bridgeport, CT
10 13 reviews
Bridgeport, CT
01/08 – 03/08
$1271/nighttotal: $2542 (2 )

Renovated Cape Near Beach, With Fire Pit And Bbq, 1 Mile To Nyc Train

3 2
apartment, Fairfield
This Fairfield holiday home, minutes from Fairfield town centre and Sacred Heart University, offers easy access to Jennings and Penfield beaches, the Norwalk Aquarium, and Beardsley Zoo.
Sleeping up to ten guests, this five-bedroom, two-bathroom property boasts a fully equipped kitchen, outdoor patio with BBQ and fire pit, driveway parking for three cars, plus free on-street parking, and provides beach essentials.
Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min To Nyc - Bridgeport, CT
9.7 3 reviews
Bridgeport, CT
29/07 – 07/08
$869/nighttotal: $7821 (9 )

Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min To Nyc

3 2
house, Fairfield
This charming cottage is located in Fairfield, just 18 kilometres from Silver Sands State Park, 22 kilometres from Connecticut Post Mall Shopping Centre, and 32 kilometres from The Yale Bowl, offering a peaceful retreat away from the hustle and bustle. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The cottage features three bedrooms and one bathroom, spanning 130 square metres and comfortably accommodating up to six guests. It boasts a fully equipped kitchen, private patio, air conditioning, complimentary Wi-Fi, and private parking, along with a garden and outdoor play equipment for families.
Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Bridgeport, CT
8.8 10 reviews
Bridgeport, CT
13/11 – 15/11
$3085/nighttotal: $6170 (2 )

Charming Colonial For Events! Perfect For Family Reunions And Group Getaways!

6 10
apartment, Bridgeport
This six-bedroom, four-bathroom house, situated in Bridgeport's Downtown South Historic District near Perry House, offers easy access to attractions such as Beardsley Zoo and the Bridgeport Bluefish Baseball Club (distances not specified).
The 3,300 sq ft (approximately 307 sq m) property sleeps 8-12 guests and includes a modern master suite with a private terrace, a den, stainless steel appliances, off-street parking for six cars, and extensive outdoor space including a half-acre lawn.

Best Bridgeport, CT vacation rentals with parking

Charming Home In Seaside - Bridgeport, CT
8.4 5 reviews
Bridgeport, CT
29/07 – 07/08
$484/nighttotal: $4356 (9 )

Charming Home In Seaside

4 2
apartment, Bridgeport
This 4-bedroom house in Bridgeport is situated a mere 5-minute walk from the Amphitheatre and 10 minutes from the Bridgeport Ferry, offering excellent walkability and convenient car access within the district.
This 110 square meter property accommodates up to 7 guests with 1 king, 1 queen, and 3 twin beds, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, and garden access, with nearby attractions including Beardsley Zoo and Discovery Museum.
Familyfriendly 5br Home W/yard Theater By Li Ferry - Bridgeport, CT
9.4 117 reviews
Bridgeport, CT
23/12 – 06/01
$704/nighttotal: $9856 (14 )

Familyfriendly 5br Home W/yard Theater By Li Ferry

1 4
apartment, Bridgeport
This apartment is conveniently located in Bridgeport, close to landmarks like Webster Arena, Sacred Heart University, and Yale, making it a great base for exploring the city and its surrounding areas. The apartment has received excellent ratings for cleanliness and user experience, and a very good rating for its location.
The apartment offers a comfortable living space with a fully equipped kitchen and a modern bathroom. It also includes amenities such as air conditioning, a garden, parking, and high-speed Wi-Fi, ensuring a pleasant and convenient stay.
Indulge In Prime Luxury 3br 3-7 Guest - Bridgeport, CT
9.6 17 reviews
Bridgeport, CT
23/12 – 06/01
$852/nighttotal: $11928 (14 )

Indulge In Prime Luxury 3br 3-7 Guest

1 4
house, Bridgeport
This house is conveniently located in Bridgeport, just a short distance from major hospitals, universities, and transport hubs. It has excellent user, location, and cleanliness ratings, making it a great choice for travellers.
The house is spacious and can comfortably accommodate up to 7 guests. It offers a range of modern amenities, including a fully equipped kitchen, a Samsung 85” TV, and a smart night table with a built-in refrigerator drawer, Bluetooth speakers, LED lighting, and charging ports.
Bright, Airy Singlefamily Home In Fairfield, Minutes From Fairfield Beach - Bridgeport, CT
10 1 review
Bridgeport, CT
23/12 – 06/01
$727/nighttotal: $10178 (14 )

Bright, Airy Singlefamily Home In Fairfield, Minutes From Fairfield Beach

4 4
apartment, Fairfield
This Fairfield flat is located in the Tunxis Hill district, approximately 1.6 kilometres from Sacred Heart University and Fairfield University, and is also conveniently close to Fairfield Beach.
This 139 square metre residence accommodates up to nine guests with four bedrooms and two bathrooms, offering air conditioning, heating, a hair dryer, an iron, and a garden for outdoor enjoyment, with easy access to the Downtown Cabaret Theatre, Barnum Museum, Fairchild Wheeler Golf Course, and The Adventure Park at Discovery Museum.
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