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.

Stay At Black Rock Harbor - Bridgeport, CT
10 28 reviews

Stay At Black Rock Harbor

apartment, Bridgeport
This apartment is located in the Black Rock district of Bridgeport, a short stroll from the beach and a 10-minute drive from Fairfield University, offering a peaceful escape in a quiet neighbourhood. The apartment has excellent user ratings and is a great choice for families or groups of friends. This three-bedroom property can accommodate up to six guests, providing ample space for everyone. The apartment comes equipped with a range of amenities including a fully equipped kitchen, a sunroom, a tranquil backyard, and parking for two vehicles, including an EV charger.
Beautiful, Cozy Basement Space - Bridgeport, CT
9.7 29 reviews

Beautiful, Cozy Basement Space

apartment, Bridgeport
This Bridgeport basement apartment, sleeping two guests, offers a self-contained space with a kitchen, air conditioning, parking, and internet access.
The one-bedroom, one-bathroom flat features a modern, stylish design and is conveniently located in Bridgeport (precise location unspecified); further details are needed to determine proximity to local attractions.
Politas Place # 3 - Bridgeport, CT
9.9 84 reviews

Politas Place # 3

apartment, Bridgeport
This apartment is situated on the third floor of a property in Bridgeport, offering a peaceful stay with access to porches, a backyard, and a grill. It has consistently received excellent ratings for user experience, location, and cleanliness.
The apartment provides privacy and space for up to six guests, with an entire floor dedicated to their use. Guests can enjoy a fully equipped kitchen, laundry facilities, outdoor living spaces, and a shared backyard with a grill, making it ideal for families and groups seeking a comfortable and convenient stay in Bridgeport.
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.

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.

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.
Cozy Studio Unit - Bridgeport, CT
9.9 81 reviews

Cozy Studio Unit

apartment, Trumbull
This Trumbull studio apartment is conveniently located within a 6.4km radius of Bridgeport Hospital, Sacred Heart University, and the Trumbull Mall, offering easy access to major highways and the coast.
The self-contained unit sleeps four, features a kitchenette with fridge, freezer and microwave, plus a private backyard with gazebo, swimming pool and on-site parking; nearby attractions include the seaside beach (8km) and Yale University (14.5km).
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.
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.

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.

Beechmont - Perfect For Family Retreat! - Bridgeport, CT
No reviews

Beechmont - Perfect For Family Retreat!

house, Bridgeport
This detached property is located in the North End district of Bridgeport, a short walk from Svihra Park and St. Vincent's Medical Center, and within 3 kilometres of Glenwood Park and Beardsley Zoo.
This holiday home offers a private kitchen with a fridge, freezer, microwave oven, and dishwasher, along with air conditioning, a terrace, garden, and parking, with free WiFi available in public areas.
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.
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.
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

Family Home Near Roosevelt Forest & Historic Sites - Bridgeport, CT
8.0 1 review

Family Home Near Roosevelt Forest & Historic Sites

cottage, Stratford
This Stratford lodge is located 2.8 kilometres from the Housatonic River and 4.5 kilometres from the Connecticut Sports Center, with the historic Capt David Judson House and Great River Golf Club also within 10 kilometres.
This pet-friendly holiday home offers air conditioning, complimentary Wi-Fi in common areas, a fully equipped kitchen with a microwave and dishwasher, and on-site parking.
Modern Studio Near Fairfield & Sacred Heart Univ - Bridgeport, CT
10 90 reviews

Modern Studio Near Fairfield & Sacred Heart Univ

apartment, 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.
Walk To Beach, Seaside Park, University - Bridgeport, CT
9.5 85 reviews

Walk To Beach, Seaside Park, University

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

Luxury Family Retreat With Lake & Comfort.

apartment, Trumbull
This spacious house is located in Trumbull, just a short distance from the lake and local attractions, offering a tranquil escape from the hustle and bustle. It consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The house has six bedrooms and four bathrooms, comfortably accommodating up to twelve guests. The house also features two kitchens, two living rooms, an office, and a patio, making it perfect for families or groups looking for a relaxing getaway.

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.

Modern 3br Home | Near Downtown & Hospitals - Bridgeport, CT
No reviews

Modern 3br Home | Near Downtown & Hospitals

apartment, Bridgeport

Browse Downtown Holiday Rentals in Bridgeport, CT

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

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

Renovated 2br Retreat / Modern Comforts Included

apartment, Bridgeport
Beautiful 1-br Apt In Historic Home - Bridgeport, CT
10 4 reviews

Beautiful 1-br Apt In Historic Home

apartment, Bridgeport
Whole Private Spacious House $7k/mo Special 5bdrms - Bridgeport, CT
10 1 review

Whole Private Spacious House $7k/mo Special 5bdrms

apartment, Bridgeport
Zen, Spacious & Comfy 2 Bed, Lux Beds - Bridgeport, CT
10 2 reviews

Zen, Spacious & Comfy 2 Bed, Lux Beds

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

Landing | Stunning 1bd In Steelpointe Harbor

apartment, Bridgeport
Stay At Black Rock Harbor - Bridgeport, CT
9.9 70 reviews

Stay At Black Rock Harbor

house, 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
Nuevo Cómodo Apartamento Estudio - Bridgeport, CT
10 27 reviews

Nuevo Cómodo Apartamento Estudio

apartment, 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.

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
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