Bridgeport, Connecticut

Vacation Rentals in Bridgeport, Connecticut

Discover 47 vacation rental properties in Bridgeport. From 1 to 5 bedrooms. Average $256/night. 100% have pools.

47 verified listings Book securely on VRBO Prices updated March 2026

47 properties available

59 Rennell St, Bridgeport · Lovely 1 bedroom cozy modern apartment w/75” 4K TV

59 Rennell St, Bridgeport · Lovely 1 bedroom cozy modern apartment w/75” 4K TV

1 bed 1 bath
PoolA/CWiFiBalcony
$133/night
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Centric property close to all the great things in the city

Centric property close to all the great things in the city

2 beds 1 bath
PoolA/CWiFiBalcony
$187/night
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Cheerful 4 bedrooms residential house.

Cheerful 4 bedrooms residential house.

4 beds 2 baths
PoolA/CWiFiBalcony
$246/night
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Cozy Home Away From Home

Cozy Home Away From Home

2 beds 1 bath
PoolA/CWiFiBalcony
$70/night
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(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

2 beds 1 bath
PoolA/CWiFiBalcony
$187/night
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⭐️Warm & Cozy 🌟Studio Suite in FFLD COUNTY

⭐️Warm & Cozy 🌟Studio Suite in FFLD COUNTY

1 bed 1 bath
PoolA/CWiFiBalcony
$126/night
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Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.

3 beds 1 bath
PoolA/CWiFiBalcony
$188/night
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Catch some Zzz at Black Rock Harbor

Catch some Zzz at Black Rock Harbor

3 beds 2 baths
PoolA/CWiFiBalcony
$508/night
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Lovely 2bd close to Major Attractions!

Lovely 2bd close to Major Attractions!

2 beds 1 bath
PoolA/CWiFiBalcony
$175/night
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Beautiful Apartment Quiet Area

Beautiful Apartment Quiet Area

1 bed 1 bath
PoolA/CWiFiBalcony
$135/night
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Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.

Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.

2 beds 1 bath
PoolA/CWiFiBalcony
$250/night
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Contemporary 5-Bed Gem Your Dream Home Awaits

Contemporary 5-Bed Gem Your Dream Home Awaits

5 beds 2 baths
PoolA/CWiFiBalcony
$486/night
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Beach Cottage on the Harbor!<br>

Beach Cottage on the Harbor!<br>

4 beds 1 bath
PoolA/CWiFiBalcony
$618/night
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Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit

4 beds 2 baths
PoolA/CWiFiBalcony
$330/night
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Cozy + Sunny Coastal Apt by Long Island Sound

Cozy + Sunny Coastal Apt by Long Island Sound

2 beds
PoolA/CWiFiBalcony
$145/night
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Seaview Ave House-4BR/8PPL Retreat

Seaview Ave House-4BR/8PPL Retreat

4 beds 2 baths
PoolA/CWiFiBalcony
$356/night
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Opuluxe Spacious 4 BR Ellsworth with Jacuzzi

Opuluxe Spacious 4 BR Ellsworth with Jacuzzi

4 beds 3 baths
PoolA/CWiFiBalcony
$411/night
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Tranquil North End Bridgeport Luxe 2 Bdr unit

Tranquil North End Bridgeport Luxe 2 Bdr unit

2 beds 1 bath
PoolA/CWiFiBalcony
$249/night
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The B&W Haven 5BR Home with yard theater

The B&W Haven 5BR Home with yard theater

5 beds 2 baths
PoolA/CWiFiBalcony
$498/night
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Beautiful Waterfront home in the amazing Black Rock Area!

Beautiful Waterfront home in the amazing Black Rock Area!

3 beds 2 baths
PoolA/CWiFiBalcony
$574/night
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🔥Fairfield County Cozy cottage , super close great adventure

🔥Fairfield County Cozy cottage , super close great adventure

3 beds 2 baths
PoolA/CWiFiBalcony
$264/night
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Quintessential Cozy Haven, Brooklawn Beauty

Quintessential Cozy Haven, Brooklawn Beauty

4 beds 2 baths
PoolA/CWiFiBalcony
$582/night
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Sea Salt Cottage Retreat - 2 mins to Seaside Park

Sea Salt Cottage Retreat - 2 mins to Seaside Park

2 beds 1 bath
PoolA/CWiFiBalcony
$185/night
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Beautiful Bungalow ranch in the heart of quiet, safe, fun Black Rock!

Beautiful Bungalow ranch in the heart of quiet, safe, fun Black Rock!

3 beds 3 baths
PoolA/CWiFiBalcony
$293/night
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Cozy 2 bedroom near Bridgeport Hospital

Cozy 2 bedroom near Bridgeport Hospital

2 beds 1 bath
PoolA/CWiFiBalcony
$175/night
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Pleasant Lower Level Apartment

Pleasant Lower Level Apartment

1 bed 1 bath
PoolA/CWiFiBalcony
$121/night
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Beautiful 2 bedroom apartment in prime location of Bridgeport Connecticut

Beautiful 2 bedroom apartment in prime location of Bridgeport Connecticut

2 beds 1 bath
PoolA/CWiFiBalcony
$170/night
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Modern Apartment in Black Rock-

Modern Apartment in Black Rock-

1 bed 1 bath
PoolA/CWiFiBalcony
$201/night
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Cozy 2 bedroom near Bridgeport Hospital

Cozy 2 bedroom near Bridgeport Hospital

2 beds 1 bath
PoolA/CWiFiBalcony
$185/night
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Modern Apartment in Black Rock

Modern Apartment in Black Rock

1 bed 1 bath
PoolA/CWiFiBalcony
$211/night
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Modern 3 Bed House in Black Rock

Modern 3 Bed House in Black Rock

3 beds 1 bath
PoolA/CWiFiBalcony
$338/night
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Modern House in Black Rock

Modern House in Black Rock

3 beds 1 bath
PoolA/CWiFiBalcony
$324/night
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Modern 3-Bdrm Apt in Black Rock

Modern 3-Bdrm Apt in Black Rock

3 beds 1 bath
PoolA/CWiFiBalcony
$334/night
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Beach House located in Black Rock Harbor. Walk 1 block to beach. Private & Quiet

Beach House located in Black Rock Harbor. Walk 1 block to beach. Private & Quiet

1 bed 1 bath
PoolA/CWiFiBalcony
$331/night
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Urban Retreat Cozy Garden Apartment

Urban Retreat Cozy Garden Apartment

3 beds 1 bath
PoolA/CWiFiBalcony
$154/night
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Black Rock Bungalow

Black Rock Bungalow

1 bed 1 bath
PoolA/CWiFiBalcony
$239/night
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Cozy Getaway in Bridgeport

Cozy Getaway in Bridgeport

2 beds 1 bath
PoolA/CWiFiBalcony
$150/night
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Bridgeport Vacation Rental - Walk to Beach!

Bridgeport Vacation Rental - Walk to Beach!

3 beds 2 baths
PoolA/CWiFiBalcony
$325/night
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Charming apaertment near Yale Hosp/Bridgeport

Charming apaertment near Yale Hosp/Bridgeport

2 beds 1 bath
PoolA/CWiFiBalcony
$86/night
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Cozy Bridgeport Apartment: 2 Mi to Downtown!

Cozy Bridgeport Apartment: 2 Mi to Downtown!

1 bed 1 bath
PoolA/CWiFiBalcony
$215/night
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Captain House in Black Rock-Academic Rental

Captain House in Black Rock-Academic Rental

3 beds 2 baths
PoolA/CWiFiBalcony
$351/night
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Sunny + Spacious Condo - 5 mins walk to the water

Sunny + Spacious Condo - 5 mins walk to the water

3 beds 1 bath
PoolA/CWiFiBalcony
$175/night
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Entire lovely & private first floor unit

Entire lovely & private first floor unit

2 beds 1 bath
PoolA/CWiFiBalcony
$103/night
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Newly Renovated Lux Second Floor Apartment

Newly Renovated Lux Second Floor Apartment

2 beds 1 bath
PoolA/CWiFiBalcony
$166/night
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THIRD FLOOR LOFT STYLE APARTMENT

THIRD FLOOR LOFT STYLE APARTMENT

2 beds 1 bath
PoolA/CWiFiBalcony
$150/night
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Comfy & Cozy 2-bedroom 1st-fl unit. Near Bpt Hosp!

Comfy & Cozy 2-bedroom 1st-fl unit. Near Bpt Hosp!

2 beds 1 bath
PoolA/CWiFiBalcony
$175/night
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Entire First Floor Apartment in Bridgeport, CT

Entire First Floor Apartment in Bridgeport, CT

2 beds 1 bath
PoolA/CWiFiBalcony
$135/night
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