Search vacation rentals in Bridgeport, CT from 100+ sites!

276 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Bridgeport, CT vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Bridgeport, CT

Best Bridgeport, CT vacation rentals with a balcony

The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen - Bridgeport, CT
8.0 1 review
Bridgeport, CT
08/28 – 12/18
$166/nighttotal: $18592 (112 )

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

2 1
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.
Renovated Cape Near Beach With Fire Pit - Bridgeport, CT
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).
Quintessential Cozy Haven, Brooklawn Beauty - Bridgeport, CT
10 4 reviews
Bridgeport, CT
08/31 – 09/04
$522/nighttotal: $2088 (4 )

Quintessential Cozy Haven, Brooklawn Beauty

4 2
apartment , Bridgeport
This Bridgeport apartment is located in the Brooklawn - St. Vincent neighborhood, offering proximity to attractions such as Beardsley Zoo and the Downtown Cabaret Theatre.
This 4-bedroom rental sleeps up to 10 guests and includes a full kitchen with a microwave and dishwasher, air conditioning, a terrace, and complimentary Wi-Fi, making it suitable for families and pets.
Cozy Condo With Yard And Patio. Long-stay Discount Available - Bridgeport, CT
9.7 159 reviews
Bridgeport, CT
07/19 – 08/15
$286/nighttotal: $7722 (27 )

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.

Beechmont-charming Colonial For Events And Getaways! - Bridgeport, CT
8.0 1 review
Bridgeport, CT
07/19 – 08/15
$626/nighttotal: $16902 (27 )

Beechmont-charming Colonial For Events And Getaways!

6 2
house , Bridgeport
This Bridgeport house rental is located 8.5 miles from Silver Sands State Park and 12 miles from the Connecticut Post Mall, offering easy access to area attractions.
This 3300-square-foot home features one bedroom, four bathrooms, and can accommodate up to 23 guests, boasting amenities such as a fully equipped kitchen, free Wi-Fi, and private parking.
Modern 2 Bedroom Apt In The Heart Of Black Rock - Bridgeport, CT
9.3 29 reviews
Bridgeport, CT
12/23 – 01/06
$286/nighttotal: $4004 (14 )

Modern 2 Bedroom Apt In The Heart Of Black Rock

1 4
apartment , Bridgeport
This modern apartment is located in the peaceful Black Rock neighborhood, just a short distance from Bridgeport's beautiful beaches, museums, lighthouses, and parks. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
This comfortable dwelling features two bedrooms and one bathroom, comfortably accommodating up to four guests. The apartment includes a fully equipped kitchen, in-suite laundry, air conditioning, parking, and internet access, making it ideal for a relaxing and convenient stay.
Polita’s Place # 2 - Bridgeport, CT
9.9 77 reviews
Bridgeport, CT
12/23 – 01/06
$190/nighttotal: $2660 (14 )

Polita’s Place # 2

1 4
apartment , Bridgeport
This Bridgeport apartment is located on the third floor of a building, just a short walk from the waterfront and a quick drive to the city's museums and downtown area. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers a peaceful retreat from the city's hustle and bustle, with a spacious layout that can comfortably accommodate up to six guests. Enjoy a fully equipped kitchen, laundry facilities, a private backyard, and easy access to shared porches and outdoor spaces.
Luminous Retreat 5br Home, Private Yard & Pergola - Bridgeport, CT
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.

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?

    Victorian Apartment, 2-story Historic Carriage House On Estate and Come And Stay At Cozy Home 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?

    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 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?

    The best vacation 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.

Destinations nearby

Best Bridgeport, CT vacation rentals with parking

Zen, Spacious & Comfy 2 Bed, Lux Beds - Bridgeport, CT
Bridgeport, CT
08/31 – 09/04
$224/nighttotal: $896 (4 )

Zen, Spacious & Comfy 2 Bed, Lux Beds

2 2
apartment , Fairfield
This two-bedroom basement apartment rental in Bridgeport's Brooklawn-St. Vincent neighborhood offers convenient proximity to Sacred Heart and Bridgeport Hospitals.
The 2-bedroom, 1-bathroom unit sleeps 5, features a fully equipped kitchen, washer/dryer, high-speed internet, a large yard with a swing, and a new TV/soundbar; guests can enjoy nearby attractions in Fairfield.
Renovated 2br Retreat / Modern Comforts Included - Bridgeport, CT
10 2 reviews
Bridgeport, CT
06/23 – 06/25
$319/nighttotal: $638 (2 )

Renovated 2br Retreat / Modern Comforts Included

2 5
apartment , Bridgeport
This Bridgeport West Side apartment, near the Barnum Museum and Downtown Cabaret Theatre, offers easy access to Seaside Park and Beardsley Zoo.
The 900-square-foot rental features three bedrooms, one bathroom, and sleeps five, boasting a fully equipped kitchen, private backyard, and convenient self check-in.
Renovated 3br Apt / Easy Check-in / Familyfriendly - Bridgeport, CT
Bridgeport, CT
06/23 – 06/25
$311/nighttotal: $622 (2 )

Renovated 3br Apt / Easy Check-in / Familyfriendly

3 5
apartment , Bridgeport
This newly renovated three-bedroom apartment rental in Bridgeport's West End is conveniently located near the Discovery Museum's Adventure Park, South Benson Marina, and Baldwin Plaza Shopping Center, offering easy access to local attractions.
The 900-square-foot unit comfortably sleeps eight guests with three bedrooms, one bathroom, a fully equipped kitchen including a dishwasher, and a shared backyard; amenities include smart TVs, high-speed internet, and self check-in.
Spacious&gracious- 5br Fam-friendly Near I95&shops - Bridgeport, CT
8.5 4 reviews
Bridgeport, CT
06/23 – 06/25
$675/nighttotal: $1350 (2 )

Spacious&gracious- 5br Fam-friendly Near I95&shops

5 5
house , Fairfield
This Fairfield vacation home, near I-95, is conveniently located 11 miles from Silver Sands State Park and 14 miles from the Connecticut Post Mall.
This 2,000-square-foot house boasts a spacious five-bedroom layout, accommodating up to 22 guests, and features a bonus game room with a pool table, darts, and arcade games, plus a home theater with massage seating.

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.

Fairfield Favorite - Bridgeport, CT
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.
Home In Fairfield - Bridgeport, CT
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.
Business Or Weekend Escape - Bridgeport, CT
9.2 54 reviews
Bridgeport, CT
08/31 – 09/04
$139/nighttotal: $556 (4 )

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.
Spacious Cottage Loft - Bridgeport, CT
10 106 reviews
Bridgeport, CT
08/31 – 09/04
$257/nighttotal: $1028 (4 )

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.

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min Walk - Bridgeport, CT
9.4 8 reviews
Bridgeport, CT
08/31 – 09/04
$189/nighttotal: $756 (4 )

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

1 2
apartment , Bridgeport
Charming 3-bedroom Beach Cottage In Beautiful Fairfield With Ac - Bridgeport, CT
Bridgeport, CT
08/31 – 09/04
$519/nighttotal: $2076 (4 )

Charming 3-bedroom Beach Cottage In Beautiful Fairfield With Ac

3 2
cottage , Fairfield
Dune Fairfield Beach - Bridgeport, CT
Bridgeport, CT
08/31 – 09/04
$390/nighttotal: $1560 (4 )

Dune Fairfield Beach

1 2
apartment , Fairfield
Connecticut Beach Cottage On The Long Island Sound - Bridgeport, CT
9.9 71 reviews
Bridgeport, CT
08/31 – 09/04
$443/nighttotal: $1772 (4 )

Connecticut Beach Cottage On The Long Island Sound

1 2
apartment , Stratford

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.

Lovely Bohemian Loft Downtwn, Amphitheater,seaside Park,metro North,2-10min Walk - Bridgeport, CT
9.6 9 reviews
Bridgeport, CT
08/31 – 09/04
$189/nighttotal: $756 (4 )

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

1 2
apartment , Bridgeport

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.

Fairfield Favorite - Bridgeport, CT
10 18 reviews
Bridgeport, CT
12/23 – 01/06
$1596/nighttotal: $22344 (14 )

Fairfield Favorite

1 4
apartment , Fairfield
©2026 cozycozy.com