Search vacation rentals in Bridgeport, CT from 100+ sites!
276 available vacation rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Vacation rentals and Airbnb offers in Bridgeport, CT
9.3 42 reviews
Bridgeport, CT
07/29 – 08/07
$188/nighttotal: $1692 (9 )
Modern Apartment In Black Rock-
1 2
apartment , Bridgeport
This modern one-bedroom apartment is located in the quiet Black Rock neighborhood of Bridgeport, just a short distance from beautiful beaches, museums, lighthouses, and parks. It has consistently received excellent ratings for cleanliness, location, and overall user experience. The apartment comfortably accommodates up to four guests and features a fully equipped kitchen with a fridge, freezer, and microwave oven. Enjoy amenities like air conditioning, parking, internet access, and a peaceful setting perfect for relaxing after a day of exploring Bridgeport's attractions.
9.2 7 reviews
Bridgeport, CT
08/01 – 08/03
$165/nighttotal: $330 (2 )
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
1 2
apartment , Bridgeport
This pet-friendly one-bedroom apartment in downtown Bridgeport is a five-minute walk from Bridgeport Train Station and the Baldwin Plaza Shopping Center. The unit, sleeping two guests, features a kitchen with a fridge and microwave, air conditioning, free Wi-Fi, a Smart TV, on-site parking, and is near attractions like the Barnum Museum and Downtown Cabaret Theatre, plus recreational options including ice skating and swimming.
9.0 88 reviews
Bridgeport, CT
07/29 – 08/07
$92/nighttotal: $828 (9 )
Historic Brownstone Close To Beach & Amphitheater
1 2
apartment , Bridgeport
This one-bedroom garden apartment is located in a historic brownstone just a block from the Long Island Sound in Bridgeport, offering easy access to scenic walks, beaches, and waterfront activities. Guests consistently rate this rental excellent for cleanliness, location, and overall experience. The apartment is ideal for a couple seeking a quiet and comfortable stay. It features a private kitchen, bathroom, and exposed brick throughout, adding a touch of rustic charm. Guests can enjoy modern amenities while appreciating the historical significance of the building, originally constructed by P.T. Barnum in 1886.
9.5 35 reviews
Bridgeport, CT
12/23 – 01/06
$370/nighttotal: $5180 (14 )
Modern 3 Bedroom House In The Heart Of Black Rock
1 4
house , Bridgeport
This Bridgeport home is located in Black Rock, just a 5-minute walk from the beach and restaurants. It has excellent user, location, and cleanliness ratings. The 3-bedroom home comfortably sleeps 8 guests and includes a fully equipped kitchen. Enjoy amenities like air conditioning, internet, a peaceful outdoor area, and the option to bring your pets.
8.8 10 reviews
Bridgeport, CT
08/01 – 08/03
$1641/nighttotal: $3282 (2 )
Charming Colonial For Events! Perfect For Family Reunions And Group Getaways!
6 2
apartment , Bridgeport
This Bridgeport colonial home rental, located in the Downtown South Historic District near Perry House, offers easy access to Beardsley Zoo, The Discovery Museum's Adventure Park, and Fairchild Wheeler Golf Course. This 3,300-square-foot residence boasts six bedrooms, four bathrooms, off-street parking for six cars, and an expansive lawn, comfortably accommodating up to twelve guests with amenities including a microwave, air conditioning, and updated stainless steel appliances.
9.9 42 reviews
Bridgeport, CT
08/01 – 08/03
$163/nighttotal: $326 (2 )
Orange & Groovy, Ricport Studio 3, Stylish Aprtmnt
1 2
apartment , Bridgeport
This Bridgeport studio apartment is centrally located, a minute from Metro-North/Amtrak and a two-minute walk from the Port Jefferson ferry, offering easy access to the beach, a park, the amphitheater, and numerous restaurants. The pet-friendly unit (fee applies), sleeps two, includes a kitchen with a fridge and microwave, air conditioning, parking, and boasts large windows with unique views from a converted industrial building.
10 40 reviews
Bridgeport, CT
09/03 – 09/15
$110/nighttotal: $1320 (12 )
Bright, Stylish & Cozy Suite
1 2
apartment , Stratford
This Stratford suite is located in a quiet district, offering easy access to local attractions. This 1-bedroom, 1-bathroom apartment accommodates up to 5 guests with a queen bed, sofa bed, and an extra floor mattress, featuring a full kitchen, air conditioning, and parking.
Bridgeport, CT
08/01 – 08/03
$126/nighttotal: $252 (2 )
Modern Apartment In A Great Location
1 2
apartment , Bridgeport
This downtown Bridgeport apartment offers immediate access to restaurants, bars, and art venues, situated in a prime location within the city's central business district. This 3rd-floor unit, converted from an office space, accommodates up to 2 guests and features a bright bedroom with Roku TV, a compact bathroom, a fridge, air conditioning, and internet, with convenient street parking available.
9.2 54 reviews
Bridgeport, CT
09/03 – 09/15
$130/nighttotal: $1560 (12 )
Business Or Weekend Escape
1 2
apartment , Stratford
This Stratford vacation rental is located within two miles of the Housatonic River, Perry House, and the Captain David Judson House of the Stratford Historical Society. The one-bedroom, one-bathroom house sleeps four guests and includes amenities such as a Smart TV, barbecue grill, and proximity to Academy Hill and Newfield Park for outdoor recreation.
10 1 review
Bridgeport, CT
06/27 – 07/04
$445/nighttotal: $3115 (7 )
Modern 3 Bed House In Black Rock
3 2
apartment , Bridgeport
This Bridgeport vacation rental is conveniently located just a short drive from the Bridgeport Downtown South Historic District and Jennings Beach, offering easy access to both attractions and the waterfront. The home is perfect for a small family or group of friends, with 3 bedrooms and 1 bathroom in a comfortable 1510 square feet. The rental includes modern amenities like a full kitchen, washer and dryer, and air conditioning, and guests can enjoy a private garden, parking, and a comfortable living space with a Smart TV and desk.
9.6 46 reviews
Bridgeport, CT
09/03 – 09/15
$377/nighttotal: $4524 (12 )
Quintessential Cozy Haven, Brooklawn Beauty
1 2
apartment , Bridgeport
This Bridgeport apartment is conveniently located in Brooklawn, close to Fairfield University, Sacred Heart University, and the University of Bridgeport, making it ideal for travelers visiting the area. The apartment has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay. The apartment features four bedrooms and two bathrooms, comfortably accommodating up to ten guests. Guests can enjoy a fully equipped kitchen, a spacious living area, a private garden, and on-site parking, along with other amenities like air conditioning and internet access.
9.6 5 reviews
Bridgeport, CT
08/01 – 08/03
$491/nighttotal: $982 (2 )
Lrg 2 Bedroom Apart In Blackrock
2 2
apartment , Bridgeport
This Bridgeport beachfront apartment is conveniently located near Fairfield, within one mile of Longfellow and Seaside Parks, and three miles from Fairfield University and the Fairfield Museum and History Center, with Fairfield Metro Station a short 17-minute walk away. This two-bedroom, one-bathroom rental sleeps five guests and features a fully equipped kitchen with a refrigerator, oven, stovetop, microwave, and in-unit laundry, plus a TV and coffee/tea maker.
Best Bridgeport, CT vacation rentals with a balcony
10 11 reviews
Bridgeport, CT
08/01 – 08/03
$909/nighttotal: $1818 (2 )
Renovated Cape Near Beach, With Fire Pit And Bbq, 1 Mile To Nyc Train
3 2
apartment , Fairfield
This Fairfield vacation home, near Sacred Heart University and minutes from Jennings and Penfield Beaches, offers easy access to the Norwalk Aquarium and Beardsley Zoo. This five-bedroom, two-bathroom house sleeps ten, features a fully equipped kitchen, outdoor patio with BBQ, Roku smart TVs, fast Wi-Fi, driveway parking for three cars, and pet-friendly accommodations for dogs under 30 pounds.
This fully furnished apartment is located in the Brooklawn - St. Vincent neighborhood of Bridgeport, just a short distance from downtown Bridgeport, Bridgeport Hospital, and major highways for easy access to other Connecticut destinations. The property has received excellent user ratings, making it a popular choice for travelers. The 1,500 square foot apartment can comfortably accommodate up to 5 guests with its 3 bedrooms and 1 bathroom. It offers a range of amenities including a fully equipped kitchen, air conditioning, a terrace, a garden, and parking, making it a perfect choice for families or groups looking for a comfortable and convenient stay.
8.0 1 review
Bridgeport, CT
07/29 – 08/07
$308/nighttotal: $2772 (9 )
The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen
2 2
apartment , Bridgeport
This two-bedroom Bridgeport apartment rental, located in the Brooklawn-St. Vincent neighborhood, offers convenient proximity to Beardsley Zoo, the Discovery Museum, and Fairchild Wheeler Golf Course. The 2,000-square-foot residence features a fully equipped kitchen, a spacious backyard, smart TVs, high-speed internet, and sleeps up to five guests comfortably.
9.7 159 reviews
Bridgeport, CT
07/29 – 08/07
$319/nighttotal: $2871 (9 )
Cozy Condo With Yard And Patio. Long-stay Discount Available
3 2
apartment , Fairfield
This Fairfield apartment is conveniently located about 10 miles from Silver Sands State Park and 13 miles from Connecticut Post Mall Shopping Center, making it a great base for exploring the area. The apartment has received excellent ratings for location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay. The spacious apartment can comfortably accommodate up to 6 guests in its 3 bedrooms and 2 bathrooms. Guests can enjoy a private patio and yard, a fully equipped kitchen with a dishwasher, and access to free parking and Wi-Fi.
Guest-Favorite Family Vacation Rentals in Bridgeport, CT
These family-friendly vacation rentals in Bridgeport, CT offer spacious layouts and easy access to local beaches.
9.7 84 reviews
Bridgeport, CT
12/23 – 01/06
$704/nighttotal: $9856 (14 )
Luminous Retreat 5br Home, Private Yard & Pergola
1 4
apartment , Fairfield
This 5-bedroom apartment in Fairfield is perfect for large families or groups of up to 12 people. It has received excellent ratings for its location, cleanliness, and user experience. The apartment is fully equipped with a kitchen, air conditioning, and a garden. It also has parking and internet access. Guests can enjoy the nearby attractions, such as the Fairfield Museum and History Center, which is just a short walk away.
9.6 143 reviews
Bridgeport, CT
09/03 – 09/15
$420/nighttotal: $5040 (12 )
Southport Shoreline Charm: Elegant Coastal Escape
1 2
apartment , Fairfield
This Fairfield accommodation is a 3-bedroom, 2-bathroom home situated just minutes from the town center and beaches. It has an excellent user rating and is family-friendly, with amenities like a ping-pong table and outdoor patio with a grill. The home has a floor area of 100 square feet and can accommodate up to 7 guests. It features cozy living areas, a fully stocked kitchen, and two full bathrooms. Amenities include sound machines in all bedrooms, two monitors and a docking station in the first bedroom, a coffee maker, and a washer and dryer.
10 18 reviews
Bridgeport, CT
12/23 – 01/06
$1596/nighttotal: $22344 (14 )
Fairfield Favorite
1 4
apartment , Fairfield
This Fairfield home is located on a hill, offering privacy and scenic views, and is right next to Brooklawn Country Club. The property is steeped in history, adding a unique charm to your stay. This spacious home has four bedrooms and five bathrooms, comfortably accommodating up to eight guests. The home offers a range of amenities, including a swimming pool, sauna, fitness center, and a large garden, perfect for relaxing and enjoying the beautiful Fairfield scenery.
9.4 20 reviews
Bridgeport, CT
12/23 – 01/06
$932/nighttotal: $13048 (14 )
Grand Fairfield Getaway- 5br Fam-friendly Near I95&shops - Spacious&gracious\n\n
5 4
apartment , Fairfield
This Fairfield home is conveniently located within a 3km radius of Fairfield University, Bridgeport Downtown South Historic District, and Longfellow Park, making it easy to explore the area's attractions. The property has received excellent user ratings, indicating a comfortable and enjoyable stay for guests. This 5-bedroom house can accommodate up to 12 guests, providing ample space for families or groups. The home offers a range of amenities, including a fully equipped kitchen, a garden with barbecue grills, a terrace, and a tennis court, ensuring a relaxing and entertaining stay.
Frequently Asked Questions about vacation 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, like spring and fall. The weather is still nice, but the crowds are smaller and the prices are lower. You can save money by booking your rental in advance, especially if you're traveling during peak season.
What are the best Airbnb and vacation rentals in Bridgeport, CT?
What are the best budget-friendly activities in Bridgeport, CT?
You can walk or bike along the Bridgeport Harborwalk, which offers stunning views of the Long Island Sound. You can also visit the Downtown Bridgeport area and explore the many shops and restaurants. And if you're looking for something more active, the Bridgeport Public Library offers a variety of free programs and events.
What are the most popular Airbnbs in Bridgeport, CT?
What are the best walking or cycling routes in Bridgeport, CT?
The Bridgeport Harborwalk is a great place to walk or bike, and it offers stunning views of the Long Island Sound. The Bridgeport Greenway is another great option, and it's a great way to see the city's parks and gardens.
What are the best vacation rentals with a pool in Bridgeport, CT?
Are there pet-friendly attractions in Bridgeport, CT?
The Beardsley Zoo is pet-friendly, and they have a special area for dogs. The Bridgeport Harborwalk is also pet-friendly, and it's a great place to take your dog for a walk.
What are the best rentals for families and kids in Bridgeport, CT?
What are the top sports attractions and facilities in Bridgeport, CT?
Bridgeport is home to the Webster Bank Arena, which hosts a variety of sporting events, concerts, and other entertainment. The Bridgeport Bluefish are a minor league baseball team, and they play their home games at The Ballpark at Harbor Yard. And if you're a fan of hockey, the Bridgeport Sound Tigers are a minor league hockey team, and they play their home games at Webster Bank Arena.
What are the best rentals or Airbnbs with a jacuzzi in Bridgeport, CT?
This five-bedroom Brooklawn-St. Vincent home is conveniently located a short walk from Bridgeport's Downtown South Historic District and St. Vincent's Medical Center, and within a mile of Svihra and Lafayette Parks. This 2,000-square-foot vacation rental sleeps up to 11 guests and boasts a fully equipped kitchen, free Wi-Fi, a balcony, and parking, making it ideal for families or groups visiting Bridgeport.
10 2 reviews
Bridgeport, CT
08/28 – 12/18
$154/nighttotal: $17248 (112 )
2 Mi To Dtwn: Well-appointed Bridgeport Duplex!
3 1
apartment , Bridgeport
This Bridgeport vacation rental is conveniently located near Glenwood Park, the Bridgeport Downtown South Historic District, and Svihra Park, all within 1.2 miles. This 1400-square-foot house features three bedrooms, two bathrooms, a fully equipped kitchen, and can comfortably accommodate six guests, offering free on-site parking and convenient access to St. Vincent's Medical Center and Beardsley Zoo.
Bridgeport, CT
08/01 – 08/03
$700/nighttotal: $1400 (2 )
Renovated Cape Near Beach With Fire Pit
3 2
house , Fairfield
Fairfield Retreat, a one-bedroom house in Fairfield, Connecticut, is conveniently located 11 miles from Silver Sands State Park and 14 miles from the Connecticut Post Mall. This two-bathroom home sleeps up to 17 guests and offers free Wi-Fi, private parking, a fully equipped kitchen, and a relaxing garden; enjoy easy access to shopping, beaches, and Yale University (22 miles away).
9.0 1 review
Bridgeport, CT
08/01 – 08/03
$399/nighttotal: $798 (2 )
2 Bed Apt In Blackrock By Beach
2 2
apartment , Bridgeport
This two-bedroom Bridgeport apartment, located in the desirable Black Rock neighborhood, is conveniently situated near the beach, 10 miles from Silver Sands State Park, and 14 miles from the Connecticut Post Mall. This 10,760-square-foot rental boasts a fully equipped kitchen, free Wi-Fi, air conditioning, and accommodates up to six guests, offering comfortable coastal living with easy access to area attractions.
Neighborhoods and points of interest in Bridgeport, CT
Check Out Vacation Rentals with a Pool in Bridgeport, CT
Choose a vacation rental with a pool in Bridgeport, CT to perfectly complement your day of adventures.
9.5 29 reviews
Bridgeport, CT
12/23 – 01/06
$650/nighttotal: $9100 (14 )
Bright Zen Studio
1 4
apartment , Fairfield
This Fairfield apartment is located on a quiet street, just a block from the lively town center, where you'll find shops, restaurants, and the train station. It has received excellent ratings for location, cleanliness, and user experience. This vacation rental offers three bedrooms and is perfect for families or groups of friends. Enjoy the private and spacious layout, the beach-inspired decor, and the outdoor oasis with a swimming pool, garden, and patio.
10 6 reviews
Bridgeport, CT
12/23 – 01/06
$695/nighttotal: $9730 (14 )
Lovely Home By The Beach In Coveted Lordship
1 4
apartment , Stratford
This Lordship, Connecticut vacation home is a two-minute walk from the beach, five minutes from waterfront restaurants, and ten minutes from Stratford train station and the Port Jefferson ferry. This three-bedroom, one-and-a-half-bathroom house sleeps six, features a heated saltwater pool, private golf cart, and access to beach equipment, plus nearby golf, tennis, and pickleball courts.
10 5 reviews
Bridgeport, CT
09/03 – 09/15
$901/nighttotal: $10812 (12 )
Home In Fairfield
1 2
apartment , Fairfield
This modern home in Fairfield is conveniently located less than a mile from the freeway exit and Metro North station, placing you within easy reach of both New York City and local attractions. The town center, shopping, and restaurants are just a 10-minute walk away. This 5-bedroom, 3-bathroom house comfortably accommodates up to 10 guests. The home offers a range of amenities, including a fully equipped kitchen, a private pool, a fenced-in backyard, and a fitness center, ensuring a comfortable and enjoyable stay for families and groups.
10 106 reviews
Bridgeport, CT
09/03 – 09/15
$238/nighttotal: $2856 (12 )
Spacious Cottage Loft
1 2
apartment , Bridgeport
The Spacious Cottage Loft is located in Black Rock, a historic seaside neighborhood in Bridgeport, just a short distance from the city's downtown area and attractions. This charming cottage has received excellent ratings for its location, cleanliness, and overall experience. The cottage has a spacious kitchen and living area, a separate sleeping area with a queen-size bed, and a private patio, perfect for relaxing and enjoying the outdoors. The cottage also offers amenities such as a swimming pool, off-street parking, a music space, and a comfortable outdoor area, making it an ideal choice for travelers looking for a peaceful and enjoyable stay.
Discover Vacation Rentals by the Sea in Bridgeport, CT
Relax near the shore in these coastal Bridgeport, CT vacation rentals, combining comfortable amenities with beautiful seaside scenery just moments away.
9.8 74 reviews
Bridgeport, CT
07/29 – 08/07
$195/nighttotal: $1755 (9 )
Victorian Apartment
1 2
apartment , Bridgeport
9.6 9 reviews
Bridgeport, CT
08/01 – 08/03
$206/nighttotal: $412 (2 )
Lovely Bohemian Loft Downtwn, Amphitheater,seaside Park,metro North,2-10min Walk
1 2
apartment , Bridgeport
10 2 reviews
Bridgeport, CT
07/29 – 08/07
$313/nighttotal: $2817 (9 )
Cozy 1920s Beach Cottage
1 2
apartment , Fairfield
9.9 105 reviews
Bridgeport, CT
07/29 – 08/07
$361/nighttotal: $3249 (9 )
Cape On The Water
2 2
apartment , Bridgeport
Discover 5-Star Vacation Rentals in Bridgeport, CT
Indulge in a luxury vacation rental in Bridgeport, CT, where high-end design meets world-class 5-star comfort.
10 26 reviews
Bridgeport, CT
09/03 – 09/15
$234/nighttotal: $2808 (12 )
Lake Hills Suite
1 2
apartment , Fairfield
Best Vacation Rentals with a Steam Room in Bridgeport, CT
Elevate your wellness routine with a vacation rental featuring a sauna in Bridgeport, CT , ideal for a restorative end to your day.
