Holiday Rentals in Bridgeport, CT

276 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Bridgeport, CT holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

276 Holiday rentals and Airbnb in Bridgeport, CT

Best family friendly Bridgeport, CT holiday rentals

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

Stay At Black Rock Harbor - Bridgeport, CT
10 69 reviews
Bridgeport, CT
23/12 – 06/01
684 €/nighttotal: 9576 € (14 )

Stay At Black Rock Harbor

3 4
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.
Cozy Cottage With Fire Pit, Near Beach, 1 Mile To Nyc Train - Bridgeport, CT
10 36 reviews
Bridgeport, CT
29/07 – 07/08
656 €/nighttotal: 5904 € (9 )

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.
Golden Colonial Home - Bridgeport, CT
9.6 200 reviews
Bridgeport, CT
23/12 – 06/01
313 €/nighttotal: 4382 € (14 )

Golden Colonial Home

1 4
apartment , Bridgeport
This two-bedroom apartment is situated in a central Bridgeport neighbourhood, just minutes from Seaside Park Beach, Jennings Beach, and Saint Mary's by the Sea, offering easy access to the city's attractions and natural beauty. It has received excellent ratings for location, cleanliness, and user experience, making it a great choice for travellers looking for a comfortable and well-maintained place to stay.
This flat comfortably accommodates up to six guests and features a spacious living room with a 55-inch TV and board games, a well-equipped kitchen with a dining table, and a newly renovated bathroom. Modern amenities, off-street parking, and a recording camera overlooking the entrance provide added convenience and security for guests.
Fairfield Favorite - Bridgeport, CT
10 18 reviews
Bridgeport, CT
23/12 – 06/01
1380 €/nighttotal: 19320 € (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.

Best Bridgeport, CT holiday rentals with a pool

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

4br/2.5ba Refuge Near University, Downtown & Beach - Bridgeport, CT
10 22 reviews
Bridgeport, CT
29/07 – 07/08
756 €/nighttotal: 6804 € (9 )

4br/2.5ba Refuge Near University, Downtown & Beach

1 2
apartment , Fairfield
This Fairfield property, situated in the University District, is one kilometre from the town centre and within three kilometres of Long Island Sound beaches.
The four-bedroom house, sleeping seven guests, boasts a heated saltwater pool, outdoor kitchen, and fire pit, alongside a fully equipped kitchen including a dishwasher, and is ideal for families or groups.
Lovely Home By The Beach In Coveted Lordship - Bridgeport, CT
10 6 reviews
Bridgeport, CT
23/12 – 06/01
602 €/nighttotal: 8428 € (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.
Bright Zen Studio - Bridgeport, CT
9.5 29 reviews
Bridgeport, CT
23/12 – 06/01
563 €/nighttotal: 7882 € (14 )

Bright Zen Studio

1 4
apartment , Fairfield
This Fairfield apartment is located on a quiet historic street, just a block away from the lively Post Road, offering easy access to shops, restaurants and the town centre. The property has received excellent ratings for its cleanliness, location and overall experience.
The home is spacious and designed to evoke a relaxed beach atmosphere. Guests can enjoy outdoor dining by the pool, relax in the garden, and make use of the fully equipped kitchen, which includes a dishwasher, fridge, freezer and microwave.
Business Or Weekend Escape - Bridgeport, CT
9.2 55 reviews
Bridgeport, CT
23/12 – 06/01
166 €/nighttotal: 2324 € (14 )

Business Or Weekend Escape

1 4
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.

Frequently asked questions about holiday rentals 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 seasons, in the spring or autumn. The weather is still pleasant, but the crowds are smaller and the prices are lower. You can find some great deals if you book in advance.
  • What are the best Airbnb and holiday rentals in Bridgeport, CT?

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

    Bridgeport has a lot of events and festivals throughout the year. The most popular one is the Bridgeport Summerfest, which takes place in July and features live music, food, and entertainment. There's also the Taste of Bridgeport, which is a great way to sample some of the city's best food.
  • What are the most popular Airbnbs in Bridgeport, CT?

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

    Bridgeport has plenty of free things to do. Take a walk along the boardwalk, visit the Beardsley Zoo for free on certain days, or explore the many parks and gardens in the city. You can also check out the many public art installations around the city.
  • What are the best holiday 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 holiday rentals with a pool in Bridgeport, CT.

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

    For a taste of local cuisine, check out the restaurants in the downtown area. There are plenty of places that serve up fresh seafood, like oysters and clams. You can also find some great Italian restaurants in the city.
  • 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 walking or cycling routes in Bridgeport, CT?

    The waterfront is a great place for a walk or bike ride. You can also check out the trails in the city's parks, like Seaside Park and Pleasure Beach.
  • 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 benefits of choosing a vacation rental in Bridgeport, CT?

    Vacation rentals offer more space and privacy than hotels, and you can often find them at a lower price. You'll also have access to a kitchen, which allows you to save money on meals.
  • What are the top sports attractions and facilities in Bridgeport, CT?

    Bridgeport is home to the Bridgeport Sound Tigers, a minor league hockey team. You can also check out the city's many parks and recreation centres, which offer a variety of sports activities.

Destinations nearby

Best Bridgeport, CT holiday rentals with a balcony

Cozy Condo With Yard And Patio. Long-stay Discount Available - Bridgeport, CT
9.7 162 reviews
Bridgeport, CT
29/07 – 07/08
276 €/nighttotal: 2484 € (9 )

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

3 2
apartment , Fairfield
This Fairfield apartment is conveniently located just 10 miles from Silver Sands State Park and 13 miles from the Connecticut Post Mall Shopping Center, offering a great base for exploring the area. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
This three-bedroom apartment can comfortably accommodate up to six guests. It features a fully equipped kitchen, a private patio, a garden, and free parking, making it a great choice for families or groups looking for a comfortable and convenient stay.
The B&w Haven 5br Home With Yard Theater + Office - Bridgeport, CT
8.8 9 reviews
Bridgeport, CT
23/12 – 06/01
473 €/nighttotal: 6622 € (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.
Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Bridgeport, CT
8.8 10 reviews
Bridgeport, CT
27/06 – 04/07
765 €/nighttotal: 5355 € (7 )

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

6 2
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.
The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen - Bridgeport, CT
8.0 1 review
Bridgeport, CT
29/07 – 07/08
266 €/nighttotal: 2394 € (9 )

The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen

2 2
apartment , Bridgeport
This Bridgeport apartment, situated in the Brooklawn-St. Vincent neighbourhood, offers convenient proximity to attractions such as Beardsley Zoo, the Discovery Museum, and Fairchild Wheeler Golf Course.
The 186 square metre (1999 square foot) property boasts two bedrooms, one bathroom, and sleeps five, featuring a fully equipped kitchen, smart TVs, a terrace, garden access, and high-speed internet.

Best Bridgeport, CT holiday rentals with parking

Modern 2 Bedroom In Black Rock - Bridgeport, CT
9.8 9 reviews
Bridgeport, CT
27/06 – 04/07
304 €/nighttotal: 2128 € (7 )

Modern 2 Bedroom In Black Rock

2 2
apartment , Bridgeport
This Bridgeport apartment, located in the Black Rock neighbourhood, offers easy access to local beaches and is within a reasonable driving distance (exact distances to be confirmed) of the Connecticut Audubon Birdcraft Museum and the Discovery Museum.
The two-bedroom, one-bathroom flat sleeps four guests and includes in-suite laundry facilities, a fully equipped kitchen with a fridge and microwave, air conditioning, parking, and internet access; nearby amenities include restaurants and the South Benson Marina.
Bridgeport Cozy Home - Bridgeport, CT
9.6 79 reviews
Bridgeport, CT
23/12 – 06/01
238 €/nighttotal: 3332 € (14 )

Bridgeport Cozy Home

1 4
apartment , Bridgeport
This two-bedroom flat is situated in a lively area of Bridgeport, just a short walk from the city's main attractions and a 10-kilometre drive from the beach. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment comfortably sleeps four guests and features a fully equipped kitchen, air conditioning, and parking. Guests can enjoy the convenience of Wi-Fi and benefit from the personalized touches that add to its charm.
Beautiful Home In The Town Of Fairfield. - Bridgeport, CT
10 4 reviews
Bridgeport, CT
23/12 – 06/01
454 €/nighttotal: 6356 € (14 )

Beautiful Home In The Town Of Fairfield.

4 4
apartment , Fairfield
This recently renovated four-bedroom, two-bathroom house in Fairfield is located just minutes from Sacred Heart University, offering convenient access to this major regional institution.
This fully equipped apartment accommodates up to nine guests and features a microwave oven, dishwasher, air conditioning, parking, and a backyard with a fire pit, alongside gleaming hardwood floors and cozy bedrooms.
Captain House In Black Rock-academic Rental - Bridgeport, CT
Bridgeport, CT
23/12 – 06/01
405 €/nighttotal: 5670 € (14 )

Captain House In Black Rock-academic Rental

3 4
apartment , Bridgeport
This three-bedroom flat is located in Bridgeport's historic Black Rock district, offering waterfront views of Burr Creek and situated 6 kilometres from Silver Sands State Park.
This property, spanning 33 square metres and accommodating up to seven guests, features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, parking, and a laundry room, with a check-out time of 10:00 AM.
©2026 cozycozy.com