Vacation Rentals in Bridgeport, CT

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Bridgeport, CT holiday rentals
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393 Holiday rentals and Airbnb in Bridgeport, CT

Plan Your Stay: Top Family Holiday Rentals in Bridgeport, CT

Give the kids instant backyard beach fun and plenty of room to unwind at spacious family holiday rentals in Bridgeport, CT.

Hermoso, Limpio Y Tranquilo Lugar Para Relajase - Bridgeport, CT
9.9 108 reviews

Hermoso, Limpio Y Tranquilo Lugar Para Relajase

apartment, Bridgeport
This two-bedroom, one-bathroom apartment in central Bridgeport offers convenient access to various attractions, though precise distances to specific landmarks remain unspecified.
The 2-bedroom flat sleeps four guests and includes a kitchen, air conditioning, internet access, and parking; further details on the property's size, interior, and nearby amenities are unavailable.
1 Bedroom - Bridgeport Apartment - Bridgeport, CT
9.6 19 reviews

1 Bedroom - Bridgeport Apartment

apartment, Bridgeport
This apartment is situated above a Tabernacle Church in Bridgeport, offering a unique cultural experience, especially on Sundays at 11 am and Wednesdays at 5 pm. The church's location is likely central, making it easy to explore the city.
The apartment offers a queen-size bed and a pull-out couch, comfortably sleeping up to three guests. It includes a kitchen with a fridge, freezer, and microwave oven, plus parking and internet access.
Paradise Awaits
5 Acre Estate - Sasco Hill - Bridgeport, CT
10 5 reviews

Paradise Awaits 5 Acre Estate - Sasco Hill

apartment, Fairfield
This luxury estate is situated on Sasco Hill in Fairfield, just a short walk from Sasco Beach and the Long Island Sound, offering a peaceful retreat with stunning views. The property has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The five-bedroom house comfortably sleeps up to ten guests, ideal for families or groups of friends. With an Olympic-sized swimming pool, twin cabanas, a spacious den, a martini lounge, and a dedicated children's suite, the estate provides a luxurious and comfortable stay with plenty of entertainment options.
Private Beach House - Bridgeport, CT
No reviews

Private Beach House

apartment, Milford
This family-friendly apartment in Milford is perfectly situated, just a 1-minute walk from Bayview Beach and a 10-minute walk to Gulf Beach, with Port Milford and Grassy Hill Country Club also close by.
Offering 121 square metres of space, this accommodation accommodates up to six guests with two bedrooms, one bathroom, a fully equipped kitchen, and air conditioning, complemented by a private terrace and garden, with on-site parking available.

Browse Holiday Rentals with a Pool in Bridgeport, CT

Discover holiday rentals with a pool in Bridgeport, CT and make every day a swim day.

Fantastic Cul-de-sac Retreat - Bridgeport, CT
No reviews

Fantastic Cul-de-sac Retreat

apartment, Fairfield
This expansive 349-square-metre residence is located on a peaceful cul-de-sac in a sought-after Fairfield neighbourhood, offering excellent privacy and convenient access to local amenities.
This five-bedroom, four-bathroom flat provides ample space for up to seven guests, featuring two primary suites, a fully fenced 0.19-hectare garden, a swimming pool, jacuzzi, fitness centre, and on-site parking.
House ∙ 3 Bedrooms ∙ 6 Guests - Bridgeport, CT
No reviews

House ∙ 3 Bedrooms ∙ 6 Guests

house, Fairfield
This beachfront property is located in Fairfield's Pine Creek district, offering direct access to the Long Island Sound and is a short drive from downtown Fairfield's amenities.
This three-storey residence accommodates six guests with three bedrooms and four bathrooms, featuring a private hot tub, kayaks, and paddleboards, and is close to the Pine Creek recreation area.
*Pool Open* Multi Family Retreat - Nature Spa Fire - Bridgeport, CT
9.8 8 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.
Fairfield Favorite - Bridgeport, CT
10 23 reviews

Fairfield Favorite

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.

Frequently asked questions about holiday rentals in Bridgeport, CT

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

    The Discovery Museum and Planetarium is always a hit with kids, and the Beardsley Zoo is a great place to spend a few hours. The boardwalk at Seaside Park is also a popular spot for families, with its amusement rides and playground.
  • What are the best Airbnb and holiday rentals in Bridgeport, CT?

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

    The summer months are the busiest time, so if you're looking for a good deal, it's best to book your vacation rental in the spring or autumn. If you're looking for a quieter time, you can also consider visiting in the winter.
  • What are the most popular Airbnbs in Bridgeport, CT?

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

    The Bridgeport Arts Festival is a great event for art lovers, and the Taste of Bridgeport is a popular food festival. The annual Oyster Festival in nearby Milford is also worth checking out.
  • 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 budget-friendly activities in Bridgeport, CT?

    Take a walk along the boardwalk at Seaside Park, it's free and offers stunning views of Long Island Sound. You can also visit the Beardsley Zoo for a low entry fee, and there are plenty of free concerts and events in the city throughout the year.
  • 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 restaurants with local dishes in Bridgeport, CT?

    For a taste of local seafood, check out the Lobster House on the waterfront. If you're looking for something more casual, try the Black Rock Tavern, which serves up classic American fare. For a truly unique experience, visit the Bridgeport Public Market.
  • What are the best rentals or Airbnbs with a jacuzzi in Bridgeport, CT?

    The best holiday 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 walking or cycling routes in Bridgeport, CT?

    The Pequonnock River Trail is a great option for a scenic walk or bike ride, and it runs through the heart of the city. The Seaside Park boardwalk is also a popular spot for walkers and cyclists.
  • Are there pet-friendly attractions in Bridgeport, CT?

    The Beardsley Zoo is pet-friendly, and there are plenty of dog-friendly restaurants and cafes in the city. The boardwalk at Seaside Park is also dog-friendly, but dogs must be kept on a leash.
  • What are the benefits of choosing a vacation rental in Bridgeport, CT?

    Vacation rentals offer more space and privacy than a hotel room, and they can often be a more affordable option, especially if you're travelling with a family or a group of friends.
  • What are the top sports attractions and facilities in Bridgeport, CT?

    The Webster Bank Arena is home to the Bridgeport Sound Tigers, the city's minor league hockey team. The University of Bridgeport also has a number of sports facilities, including a stadium and a swimming pool.

Popular destinations

Discover Holiday Rentals with a Balcony in Bridgeport, CT

Wake up to the soothing sight of the blue ocean right from your private rental balcony in Bridgeport, CT.

Renovated Cape Near Beach With Fire Pit - Bridgeport, CT
10 1 review

Renovated Cape Near Beach With Fire Pit

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.
4 Mi To Beach & Dtwn! Charming Fairfield Home - Bridgeport, CT
No reviews

4 Mi To Beach & Dtwn! Charming Fairfield Home

house, Fairfield
This Fairfield property is located 6 kilometres from the beach and town centre, with Silver Sands State Park 16 kilometres away and the Yale Bowl 31 kilometres away.
This residence offers 139 square metres of living space with four bedrooms and two bathrooms, accommodating up to 17 guests and featuring a fully equipped kitchen, air conditioning, a garden, and private parking.
Renovated Cape Near Beach, With Fire Pit And Bbq, 1 Mile To Nyc Train - Bridgeport, CT
10 18 reviews

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

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.
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.

Best Bridgeport, CT holiday rentals with parking

Modern 3-bdrm Apt In Black Rock - Bridgeport, CT
9.4 3 reviews

Modern 3-bdrm Apt In Black Rock

apartment, Bridgeport
This Bridgeport beachfront apartment, near Fairfield, is less than 2km from Longfellow and Seaside Parks and within 5km of Fairfield Museum and History Centre and Fairfield University.
The 111 square metre property boasts four bedrooms, one bathroom, sleeps ten guests, and includes a fully equipped kitchen, in-unit laundry, and on-site parking.
Seaview Ave 4br House - Sleeps 8 - Bridgeport, CT
9.9 49 reviews

Seaview Ave 4br House - Sleeps 8

house, Bridgeport
Seaview House, a four-bedroom property in Bridgeport, Connecticut, is located near the water, a short 8km drive from Seaside Park and within easy reach of Bridgeport's Metro-North station.
This self-catering house sleeps eight guests, boasting a fully equipped kitchen with stainless steel appliances, three car parking spaces, and multiple large-screen TVs throughout its living areas.
20% New Property Sale - Family-friendly Gem  Walk To Town & Train  Fully Renovated Victorian - Bridgeport, CT
10 2 reviews

20% New Property Sale - Family-friendly Gem Walk To Town & Train Fully Renovated Victorian

apartment, Milford
This five-bedroom, two-bathroom flat is located near the duck pond, a short walk from Milford town centre and 2.2 kilometres from the beach.
This property accommodates up to ten guests and offers a high-end kitchen, a fenced garden with seating, and an optional EV Level 2 charging station.
Luxury Designer 3 Bedroom ( Office) Vacation Home. - Bridgeport, CT
9.6 29 reviews

Luxury Designer 3 Bedroom ( Office) Vacation Home.

apartment, Bridgeport
This two-bedroom apartment is conveniently located in Bridgeport, within walking distance of Bridgeport Hospital and local amenities, and a short drive from downtown Bridgeport, Fairfield, New Haven, and Stamford. The accommodation has received excellent ratings for cleanliness and user experience, with a good location rating.
The apartment is spacious and comfortable, accommodating up to four guests, and features a living room, dining room, kitchen, bathroom, and front and back porches. The apartment comes fully equipped with fresh linens, towels, travel essentials, smart TVs, Wi-Fi, coffee, tea, and snacks, ensuring a comfortable and convenient stay.

Escape to the Coast: Luxury Holiday Rentals in Bridgeport, CT

Live the ultimate tropical fantasy in properties boasting high-end coastal architecture and absolute privacy at luxury holiday rentals in Bridgeport, CT.

Lrg 2 Bedroom Apart In Blackrock - Bridgeport, CT
9.4 6 reviews

Lrg 2 Bedroom Apart In Blackrock

apartment, Bridgeport

Browse Downtown Holiday Rentals in Bridgeport, CT

Find holiday rentals in the heart of Bridgeport, CT close to shops and beaches.

Luxury Designer 2 Bedroom+office/3bed Vacation Home. - Bridgeport, CT
9.6 27 reviews

Luxury Designer 2 Bedroom+office/3bed Vacation Home.

apartment, Bridgeport
Modern & Stylish 2br W/ 2 King Beds & Full Kitchen - Bridgeport, CT
9.1 105 reviews

Modern & Stylish 2br W/ 2 King Beds & Full Kitchen

apartment, Bridgeport
3br Family Apt, Renovated With Easy Check-in - Bridgeport, CT
9.4 56 reviews

3br Family Apt, Renovated With Easy Check-in

apartment, Bridgeport
The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen - Bridgeport, CT
9.0 2 reviews

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

apartment, Bridgeport

Browse Coastal Holiday Rentals in Bridgeport, CT

Open your glass doors and step directly from your living room onto the warm sand at seashore holiday rentals in Bridgeport, CT.

Bay View Beach Coastal Cottage Steps From Private Beach - Bridgeport, CT
10 4 reviews

Bay View Beach Coastal Cottage Steps From Private Beach

apartment, Milford
Orange & Groovy, Ricport Studio 3, Stylish Aprtmnt - Bridgeport, CT
9.9 49 reviews

Orange & Groovy, Ricport Studio 3, Stylish Aprtmnt

apartment, Bridgeport
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min Walk - Bridgeport, CT
9.4 8 reviews

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min Walk

apartment, Bridgeport
Charming 3-bedroom Beach Cottage In Beautiful Fairfield With Ac - Bridgeport, CT
No reviews

Charming 3-bedroom Beach Cottage In Beautiful Fairfield With Ac

cottage, Fairfield

Browse Holiday Rentals with a Hot Tub in Bridgeport, CT

Watch the sun set over the water while soaking in a steaming outdoor hot tub at island holiday rentals in Bridgeport, CT.

Luxury Family Retreat With Lake & Comfort. - Bridgeport, CT
9.7 44 reviews

Luxury Family Retreat With Lake & Comfort.

apartment, Trumbull
Laurel Beach-milford - Bridgeport, CT
9.4 15 reviews

Laurel Beach-milford

apartment, Milford
The House Haven - Bridgeport, CT
10 1 review

The House Haven

apartment, Stratford
*Pool Open* Designer Home  Hot Tub & Fire Pits - Bridgeport, CT
9.7 22 reviews

*Pool Open* Designer Home Hot Tub & Fire Pits

house, Fairfield
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