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.

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.
Bright 3-bedroom House With Ample Parking & Patio! - Bridgeport, CT
9.7 127 reviews

Bright 3-bedroom House With Ample Parking & Patio!

apartment, Fairfield
This fully renovated apartment is situated in a peaceful Fairfield neighbourhood, just 7km from Sacred Heart University and 10km from Fairfield University. The property has received excellent ratings for location, cleanliness, and user experience.
The apartment has three bedrooms and two bathrooms, accommodating up to six guests. The property is equipped with modern amenities including central air conditioning, a washing machine and dryer, a dishwasher, and strong Wi-Fi, as well as a large back patio with a fire pit.
Cozy Cottage By The Beach - Bridgeport, CT
10 6 reviews

Cozy Cottage By The Beach

apartment, Stratford
This delightful Stratford cottage enjoys a peaceful location in a quiet beach neighbourhood, conveniently close to Stratford train station and the I-95 highway.
Sleeping six guests across three bedrooms and two bathrooms, this self-catering holiday home boasts a fully equipped kitchen, air conditioning, a garden, and on-site parking, plus excellent guest reviews.
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.

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.

Business Or Weekend Escape - Bridgeport, CT
9.2 59 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.
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.
Spacious Cottage Loft - Bridgeport, CT
10 113 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.
Quaint Private Two Bdrm With Balcony, Stream View! - Bridgeport, CT
9.3 15 reviews

Quaint Private Two Bdrm With Balcony, Stream View!

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.

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.

Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Bridgeport, CT
8.8 10 reviews

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

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.
Cozy Cottage With Fire Pit - Bridgeport, CT
No reviews

Cozy Cottage With Fire Pit

chalet, Fairfield
This lodge in Fairfield is located approximately 3 kilometres from Fairfield University, the Regina A. Quick Centre for the Arts, and the Bellarmine Museum of Art, with Longfellow Park and South Benson Marina situated around 5 kilometres away.
This chalet offers complimentary Wi-Fi in common areas, free self-parking, on-site laundry facilities, a garden, gas barbecue, a picnic area, and a lobby fireplace, making it a suitable option for those seeking accommodation with amenities and proximity to educational and cultural sites.
Luxury Designer 2 Bedroom+office/3bed Vacation Home. - Bridgeport, CT
9.6 27 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.
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

Cheerful 4 Bedroom Home, In Quite Neighborhood - Bridgeport, CT
9.0 2 reviews

Cheerful 4 Bedroom Home, In Quite Neighborhood

apartment, Bridgeport
This four-bedroom house is located in the North End of Bridgeport, just a short distance from restaurants, movie theatres, Seaside Park, beaches and the downtown area. It has consistently received excellent ratings for location, cleanliness and overall user experience.
The house is spacious and comfortably sleeps six guests, with a fully equipped kitchen and a laundry room. Amenities include air conditioning, off-street parking, a private garden, and access to the basement.
Cozy Private Suite Near Train To Nyc - Bridgeport, CT
9.5 55 reviews

Cozy Private Suite Near Train To Nyc

apartment, Fairfield
This Fairfield flat offers a private suite with a separate entrance, featuring one bedroom, a living room, and a full bathroom, conveniently located within 500 meters of the Metro-North train station for easy commuting to New York City.
This accommodation provides on-site parking, air conditioning, and in-suite amenities including Netflix, a mini fridge, and a microwave, making it ideal for up to two guests seeking relaxation and exploration of downtown Fairfield's restaurants, shops, and the beach.
Charming Studio Retreat | Near Transit & Beaches - Bridgeport, CT
10 4 reviews

Charming Studio Retreat | Near Transit & Beaches

apartment, Stratford
This studio flat is located in a quiet Stratford residential area, offering a 1-minute drive to the I-95 and a 5-minute drive to Metro-North for easy access to New York City, and is also conveniently close to beaches and educational institutions like Yale and Fairfield University. Guests can enjoy hotel-style amenities in the prepared basement space, which includes fast WiFi, air conditioning, a kitchen with a fridge, freezer, and microwave oven, and free street parking, with the property being pet-friendly and boasting excellent user, location, and cleanliness ratings for up to two guests.
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.

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.

Landing | Amazing 2bd In Steelpointe Harbor - Bridgeport, CT
No reviews

Landing | Amazing 2bd In Steelpointe Harbor

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
Charming Home In Seaside - Bridgeport, CT
8.8 8 reviews

Charming Home In Seaside

apartment, Bridgeport
Lux Modern Loft ,Ricport Studio 1 Peaceful Stay - Bridgeport, CT
9.7 40 reviews

Lux Modern Loft ,Ricport Studio 1 Peaceful Stay

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

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.

Landing | Beautiful 1bd In Steelpointe Harbor - Bridgeport, CT
No reviews

Landing | Beautiful 1bd In Steelpointe Harbor

apartment, Bridgeport
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min - Bridgeport, CT
9.6 12 reviews

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

apartment, Bridgeport
Stareway To Heaven In Fairfield - Bridgeport, CT
No reviews

Stareway To Heaven In Fairfield

house, Fairfield
Stay At Black Rock Harbor - Bridgeport, CT
8.7 3 reviews

Stay At Black Rock Harbor

house, Bridgeport

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.

House ∙ 3 Bedrooms ∙ 6 Guests - Bridgeport, CT
No reviews

House ∙ 3 Bedrooms ∙ 6 Guests

house, Fairfield
Soothing Carriage House With Hot Tub In Charming Stratford - Bridgeport, CT
10 11 reviews

Soothing Carriage House With Hot Tub In Charming Stratford

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

Luxury Family Retreat With Lake & Comfort.

apartment, Trumbull
Exclusive Waterfront With Charming Italian Decor - Bridgeport, CT
No reviews

Exclusive Waterfront With Charming Italian Decor

apartment, Stratford
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