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.

Beautiful Beach Escape In Fairfield - Bridgeport, CT
9.0 4 reviews

Beautiful Beach Escape In Fairfield

apartment, Fairfield
This Fairfield apartment is just a two-minute walk from the town centre and a short distance from the beach, making it ideal for exploring the area. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property is spacious, with four bedrooms and four bathrooms, comfortably accommodating up to eight guests. It features a well-equipped kitchen, a swimming pool, a garden, and a fitness centre, ensuring a comfortable and enjoyable stay.
Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min To Nyc - Bridgeport, CT
9.5 4 reviews

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

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.
Nuevo Cómodo Apartamento Estudio - Bridgeport, CT
10 25 reviews

Nuevo Cómodo Apartamento Estudio

apartment, Bridgeport
This Bridgeport studio apartment, situated in the East End, offers easy access to I-95 (under 2km), Metro-North (under 2.5km), the Bridgeport Ferry (under 3km), Steelpointe Harbor (under 2.5km), and the Hartford Health Amphitheatre/Total Mortgage Arena, all within a 4km radius of Bridgeport city centre.
The self-contained unit, sleeping up to four guests, features a fridge, microwave, air conditioning, parking, and Wi-Fi; its private entrance on the third floor ensures peace and quiet.
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.

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.

Home In Fairfield - Bridgeport, CT
9.8 13 reviews

Home In Fairfield

apartment, Fairfield
This modern house is located in Fairfield, just a short distance from the town centre and a kilometre from the freeway exit and Metro North station. The area is quiet and residential, with easy access to shops, restaurants and amenities.
This five-bedroom property can comfortably accommodate up to ten guests. The house includes a fully equipped kitchen, a spacious living area, a private garden and a swimming pool. Guests can enjoy a range of amenities, including a fitness centre, a games room, a barbecue area and a mudroom with direct access to the pool.
Fairfield! 5 Bedroom, 3.5 Bath On Cul-de-sac - Bridgeport, CT
10 52 reviews

Fairfield! 5 Bedroom, 3.5 Bath On Cul-de-sac

apartment, Fairfield
This spacious, renovated apartment in Fairfield is conveniently located just a short distance from the town centre, universities, and transportation to NYC Grand Central. The apartment boasts excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The apartment has 5 bedrooms and 3 bathrooms, comfortably accommodating up to 12 guests. Amenities include a private heated pool, a well-equipped kitchen, a spacious living area, a family room with a large TV, and a fully furnished garden with outdoor furniture.
The House Haven - Bridgeport, CT
10 1 review

The House Haven

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.
Fairfield Old Post Road-heated Pool & Guest Cottage-walk To Nyc Train And Beach! - Bridgeport, CT
9.9 62 reviews

Fairfield Old Post Road-heated Pool & Guest Cottage-walk To Nyc Train And Beach!

apartment, Fairfield
This six-bedroom English Tudor house is situated on a prestigious street of historic homes, just 400 metres from Penfield Beach and within easy walking distance of Fairfield's town centre. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This spacious home spans 297 square metres and comfortably accommodates up to 14 guests. The house features a private heated pool, a fully equipped cottage, a designer kitchen, a formal living room with a fireplace, a garden, and a tennis court, offering a range of amenities and activities for families and groups.

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.

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
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.
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.
Beechmont-charming Colonial For Events And Getaways! - Bridgeport, CT
8.0 1 review

Beechmont-charming Colonial For Events And Getaways!

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.
Charming &Spacious 3bd, 1ba, Fam-friendly-yard&porch - Bridgeport, CT
10 3 reviews

Charming &Spacious 3bd, 1ba, Fam-friendly-yard&porch

apartment, Fairfield
This Fairfield West End apartment, conveniently located near Beardsley Zoo and the Discovery Museum, offers easy access to Fairfield's attractions.
The 93 square metre (1000 square foot) property sleeps seven guests across four bedrooms and one bathroom, boasting a fully equipped kitchen, garden, terrace, parking, and a bonus games room (additional fee applies) featuring a pool table, darts, arcade game, and table football.

Best Bridgeport, CT holiday rentals with parking

Nathalys Place! - Bridgeport, CT
9.8 32 reviews

Nathalys Place!

apartment, Bridgeport
This 2-bedroom, 1-bathroom flat is located in a Bridgeport district known for its natural light and proximity to nature, with specific distances to local landmarks yet to be detailed.
This family-friendly apartment accommodates up to 5 guests and features air conditioning, internet, and a kitchen equipped with a fridge and microwave, offering a unique ambiance and a serene, nature-infused stay.
Luxury Designer 2 Bedroom+office/3bed Vacation Home. - Bridgeport, CT
9.6 26 reviews

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

apartment, Bridgeport
This three-bedroom flat is located in the Brooklawn-St. Vincent neighbourhood of Bridgeport, just a short distance from downtown and major highways. It has received excellent user ratings and is ideal for families or groups of friends.
The apartment spans 139 square metres and comfortably accommodates up to five guests. It is fully furnished and features a modern kitchen, a private terrace, a garden, and parking, making it a perfect choice for those looking for a comfortable and convenient stay in Bridgeport.
Familyfriendly 5br Home W/yard Theater By Li Ferry - Bridgeport, CT
9.4 126 reviews

Familyfriendly 5br Home W/yard Theater By Li Ferry

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.
2bdfairfield Work & Relax Space W. Patio+fast Wifi - Bridgeport, CT
9.8 101 reviews

2bdfairfield Work & Relax Space W. Patio+fast Wifi

apartment, Fairfield
This two-bedroom flat is located in a peaceful residential area in Fairfield, just a short distance from the bustling town centre. The property has received excellent ratings for its cleanliness, location, and overall experience.
The apartment comfortably accommodates up to five guests and features a spacious living area, a fully equipped kitchen, and a private garden. Guests can enjoy a range of amenities including a fire pit, a picnic table, multiple patios, and a modern entertainment system.

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.

Bridgeport Cozy Home - Bridgeport, CT
9.6 83 reviews

Bridgeport Cozy Home

apartment, Bridgeport

Browse Downtown Holiday Rentals in Bridgeport, CT

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

Lavish Retreat Near Downtown - Bridgeport, CT
9.7 91 reviews

Lavish Retreat Near Downtown

apartment, Bridgeport
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
Pleasant Wellness Home Bridgeport-2 - Bridgeport, CT
10 3 reviews

Pleasant Wellness Home Bridgeport-2

apartment, Bridgeport
Renovated 2br Retreat / Modern Comforts Included - Bridgeport, CT
10 3 reviews

Renovated 2br Retreat / Modern Comforts Included

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.

Lovely Bohemian Loft Downtwn, Amphitheater,seaside Park,metro North,2-10min Walk - Bridgeport, CT
9.8 16 reviews

Lovely Bohemian Loft Downtwn, Amphitheater,seaside Park,metro North,2-10min Walk

apartment, Bridgeport
Qc Beach - Bridgeport, CT
9.8 26 reviews

Qc Beach

apartment, Fairfield
Seaview Ave 4br House - Sleeps 8 - Bridgeport, CT
9.9 47 reviews

Seaview Ave 4br House - Sleeps 8

house, Bridgeport
Sunrise Water Views Fairfield Ct - Bridgeport, CT
No reviews

Sunrise Water Views Fairfield Ct

apartment, 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.

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

*Pool Open* Designer Home Hot Tub & Fire Pits

apartment, Fairfield
Cozy Colonial - Private Hot Tub & Entire House - Bridgeport, CT
9.9 236 reviews

Cozy Colonial - Private Hot Tub & Entire House

house, Stratford