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Bridgeport Holiday Rentals

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49 rentals in Bridgeport.
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Live/work loft with view and exposed brick, holiday rental in Bridgeport
Live/work loft with view and exposed brick, holiday rental in Bridgeport
Live/work loft with view and exposed brick, holiday rental in Bridgeport

Live/work loft with view and exposed brick

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Beach Cottage on the Harbor; discounted weekly rental in summer, holiday rental in Bridgeport
Beach Cottage on the Harbor; discounted weekly rental in summer, holiday rental in Bridgeport
Beach Cottage on the Harbor; discounted weekly rental in summer, holiday rental in Bridgeport

Beach Cottage on the Harbor; discounted weekly rental in summer

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful 3-Story Colonial Home -10 Min. from DWTN Bridgeport, holiday rental in Bridgeport
Beautiful 3-Story Colonial Home -10 Min. from DWTN Bridgeport, holiday rental in Bridgeport
Beautiful 3-Story Colonial Home -10 Min. from DWTN Bridgeport, holiday rental in Bridgeport

Beautiful 3-Story Colonial Home -10 Min. from DWTN Bridgeport

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
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Shanz Lofts Syle Apartment, holiday rental in Bridgeport
Shanz Lofts Syle Apartment, holiday rental in Bridgeport
Shanz Lofts Syle Apartment, holiday rental in Bridgeport

Shanz Lofts Syle Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Charming and comfy  bedroom, holiday rental in Bridgeport
Charming and comfy  bedroom, holiday rental in Bridgeport
Charming and comfy  bedroom, holiday rental in Bridgeport

Charming and comfy bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 1
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Milford Beach House - New Construction!, holiday rental in Bridgeport
Milford Beach House - New Construction!, holiday rental in Bridgeport
Milford Beach House - New Construction!, holiday rental in Bridgeport

Milford Beach House - New Construction!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!, holiday rental in Bridgeport
Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!, holiday rental in Bridgeport
Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!, holiday rental in Bridgeport

Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Westport 'Gold Coast' across from Southport beach, holiday rental in Bridgeport
Westport 'Gold Coast' across from Southport beach, holiday rental in Bridgeport
Westport 'Gold Coast' across from Southport beach, holiday rental in Bridgeport

Westport 'Gold Coast' across from Southport beach

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
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Beach Cottage next to Silver Sands State Park, holiday rental in Bridgeport
Beach Cottage next to Silver Sands State Park, holiday rental in Bridgeport
Beach Cottage next to Silver Sands State Park, holiday rental in Bridgeport

Beach Cottage next to Silver Sands State Park

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
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Sea Mist Cottage... 300 steps to the beach!, holiday rental in Bridgeport
Sea Mist Cottage... 300 steps to the beach!, holiday rental in Bridgeport
Sea Mist Cottage... 300 steps to the beach!, holiday rental in Bridgeport

Sea Mist Cottage... 300 steps to the beach!

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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#2 - Your own place on the beach by Silver Sands Pk, holiday rental in Bridgeport
#2 - Your own place on the beach by Silver Sands Pk, holiday rental in Bridgeport
#2 - Your own place on the beach by Silver Sands Pk, holiday rental in Bridgeport

#2 - Your own place on the beach by Silver Sands Pk

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxe CT Country Home w/ Hi-end WiFi for WFH & School, holiday rental in Bridgeport
Luxe CT Country Home w/ Hi-end WiFi for WFH & School, holiday rental in Bridgeport
Luxe CT Country Home w/ Hi-end WiFi for WFH & School, holiday rental in Bridgeport

Luxe CT Country Home w/ Hi-end WiFi for WFH & School

Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 16
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Gem by the Sound Summ, holiday rental in Bridgeport
Gem by the Sound Summ, holiday rental in Bridgeport
Gem by the Sound Summ, holiday rental in Bridgeport

Gem by the Sound Summ

Holiday Rental House
0 bedrooms
2 bathrooms
Sleeps 4
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FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!, holiday rental in Bridgeport
FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!, holiday rental in Bridgeport
FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!, holiday rental in Bridgeport

FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beach side rental booking winter 2020\2021 Available December17 2020, holiday rental in Bridgeport
Beach side rental booking winter 2020\2021 Available December17 2020, holiday rental in Bridgeport
Beach side rental booking winter 2020\2021 Available December17 2020, holiday rental in Bridgeport

Beach side rental booking winter 2020\2021 Available December17 2020

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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#1 - A Beach Place Near Silver Sands Park, holiday rental in Bridgeport
#1 - A Beach Place Near Silver Sands Park, holiday rental in Bridgeport
#1 - A Beach Place Near Silver Sands Park, holiday rental in Bridgeport

#1 - A Beach Place Near Silver Sands Park

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront house near Silver Sands Park, holiday rental in Bridgeport
Waterfront house near Silver Sands Park, holiday rental in Bridgeport
Waterfront house near Silver Sands Park, holiday rental in Bridgeport

Waterfront house near Silver Sands Park

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Nice Duplex with view of Long Island Sound, holiday rental in Bridgeport
Nice Duplex with view of Long Island Sound, holiday rental in Bridgeport
Nice Duplex with view of Long Island Sound, holiday rental in Bridgeport

Nice Duplex with view of Long Island Sound

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Laurel Beach-Milford, holiday rental in Bridgeport
Laurel Beach-Milford, holiday rental in Bridgeport
Laurel Beach-Milford, holiday rental in Bridgeport

Laurel Beach-Milford

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming Cottage By The Sea on Fairfield Beach, holiday rental in Bridgeport
Charming Cottage By The Sea on Fairfield Beach, holiday rental in Bridgeport
Charming Cottage By The Sea on Fairfield Beach, holiday rental in Bridgeport

Charming Cottage By The Sea on Fairfield Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Bright Cottage on Silver Sands Beach, holiday rental in Bridgeport
Charming Bright Cottage on Silver Sands Beach, holiday rental in Bridgeport
Charming Bright Cottage on Silver Sands Beach, holiday rental in Bridgeport

Charming Bright Cottage on Silver Sands Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Steps To Sandy Beach on Long Island Sound, holiday rental in Bridgeport
Steps To Sandy Beach on Long Island Sound, holiday rental in Bridgeport
Steps To Sandy Beach on Long Island Sound, holiday rental in Bridgeport

Steps To Sandy Beach on Long Island Sound

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming house water views 2 houses from the clean deep sandy Private beach., holiday rental in Bridgeport
Charming house water views 2 houses from the clean deep sandy Private beach., holiday rental in Bridgeport
Charming house water views 2 houses from the clean deep sandy Private beach., holiday rental in Bridgeport

Charming house water views 2 houses from the clean deep sandy Private beach.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Elegant Beachfront, beautiful views. Come  enjoy!, holiday rental in Bridgeport
Elegant Beachfront, beautiful views. Come  enjoy!, holiday rental in Bridgeport
Elegant Beachfront, beautiful views. Come  enjoy!, holiday rental in Bridgeport

Elegant Beachfront, beautiful views. Come enjoy!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Fairfield Old Post Road with pool - walk to  NYC train and Beach, holiday rental in Bridgeport
Fairfield Old Post Road with pool - walk to  NYC train and Beach, holiday rental in Bridgeport
Fairfield Old Post Road with pool - walk to  NYC train and Beach, holiday rental in Bridgeport

Fairfield Old Post Road with pool - walk to NYC train and Beach

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Cozy getaway in Fairfield - EXPERTLY SANITIZED, holiday rental in Bridgeport
Cozy getaway in Fairfield - EXPERTLY SANITIZED, holiday rental in Bridgeport
Cozy getaway in Fairfield - EXPERTLY SANITIZED, holiday rental in Bridgeport

Cozy getaway in Fairfield - EXPERTLY SANITIZED

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning direct waterfront beach house!, holiday rental in Bridgeport
Stunning direct waterfront beach house!, holiday rental in Bridgeport
Stunning direct waterfront beach house!, holiday rental in Bridgeport

Stunning direct waterfront beach house!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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A private summer compound in Westport, CT - total seclusion yet close to it all, holiday rental in Bridgeport
A private summer compound in Westport, CT - total seclusion yet close to it all, holiday rental in Bridgeport
A private summer compound in Westport, CT - total seclusion yet close to it all, holiday rental in Bridgeport

A private summer compound in Westport, CT - total seclusion yet close to it all

Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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RENOVATED HOUSE STEPS FROM THE BEACH, holiday rental in Bridgeport
RENOVATED HOUSE STEPS FROM THE BEACH, holiday rental in Bridgeport
RENOVATED HOUSE STEPS FROM THE BEACH, holiday rental in Bridgeport

RENOVATED HOUSE STEPS FROM THE BEACH

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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#2 - Your own place on the Beach near Silver Sands Park, holiday rental in Bridgeport
#2 - Your own place on the Beach near Silver Sands Park, holiday rental in Bridgeport
#2 - Your own place on the Beach near Silver Sands Park, holiday rental in Bridgeport

#2 - Your own place on the Beach near Silver Sands Park

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beachfront Cottage w/Porch on Long Island Sound, holiday rental in Bridgeport
Beachfront Cottage w/Porch on Long Island Sound, holiday rental in Bridgeport
Beachfront Cottage w/Porch on Long Island Sound, holiday rental in Bridgeport

Beachfront Cottage w/Porch on Long Island Sound

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Westport 'Gold Coast' across from Southport beach, holiday rental in Bridgeport
Westport 'Gold Coast' across from Southport beach, holiday rental in Bridgeport
Westport 'Gold Coast' across from Southport beach, holiday rental in Bridgeport

Westport 'Gold Coast' across from Southport beach

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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#1 - A beach place by Silver Sands Park, holiday rental in Bridgeport
#1 - A beach place by Silver Sands Park, holiday rental in Bridgeport
#1 - A beach place by Silver Sands Park, holiday rental in Bridgeport

#1 - A beach place by Silver Sands Park

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A New England Jewel with Scenic Beauty, holiday rental in Bridgeport
A New England Jewel with Scenic Beauty, holiday rental in Bridgeport
A New England Jewel with Scenic Beauty, holiday rental in Bridgeport

A New England Jewel with Scenic Beauty

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront getaway walkable to restaurants and shops, holiday rental in Bridgeport
Lakefront getaway walkable to restaurants and shops, holiday rental in Bridgeport
Lakefront getaway walkable to restaurants and shops, holiday rental in Bridgeport

Lakefront getaway walkable to restaurants and shops

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks, holiday rental in Bridgeport
Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks, holiday rental in Bridgeport
Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks, holiday rental in Bridgeport

Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Walk to the beach from this modern home, holiday rental in Bridgeport
Walk to the beach from this modern home, holiday rental in Bridgeport
Walk to the beach from this modern home, holiday rental in Bridgeport

Walk to the beach from this modern home

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Available ONLY 6/23-7/4 for entire term, holiday rental in Bridgeport
Available ONLY 6/23-7/4 for entire term, holiday rental in Bridgeport
Available ONLY 6/23-7/4 for entire term, holiday rental in Bridgeport

Available ONLY 6/23-7/4 for entire term

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Brand New Laurel Beach House!, holiday rental in Bridgeport
Brand New Laurel Beach House!, holiday rental in Bridgeport
Brand New Laurel Beach House!, holiday rental in Bridgeport

Brand New Laurel Beach House!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beach house 3 BR/3&1/half bath home with private beach in CT., holiday rental in Bridgeport
Beach house 3 BR/3&1/half bath home with private beach in CT., holiday rental in Bridgeport
Beach house 3 BR/3&1/half bath home with private beach in CT., holiday rental in Bridgeport

Beach house 3 BR/3&1/half bath home with private beach in CT.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Nature Lovers Perfect Location, an hour from Manhattan, holiday rental in Bridgeport
Nature Lovers Perfect Location, an hour from Manhattan, holiday rental in Bridgeport
Nature Lovers Perfect Location, an hour from Manhattan, holiday rental in Bridgeport

Nature Lovers Perfect Location, an hour from Manhattan

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, holiday rental in Bridgeport
Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, holiday rental in Bridgeport
Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, holiday rental in Bridgeport

Summer Rental: 4 Car Garage 1/4 mile to town of Fairfeild Center

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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PRIVATE AIRY SUMMER HOME in Minutes from the BEACH and more (WESTPORT), holiday rental in Bridgeport
PRIVATE AIRY SUMMER HOME in Minutes from the BEACH and more (WESTPORT), holiday rental in Bridgeport
PRIVATE AIRY SUMMER HOME in Minutes from the BEACH and more (WESTPORT), holiday rental in Bridgeport

PRIVATE AIRY SUMMER HOME in Minutes from the BEACH and more (WESTPORT)

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Large Studio by the Beach w/private entrance, holiday rental in Bridgeport
Large Studio by the Beach w/private entrance, holiday rental in Bridgeport
Large Studio by the Beach w/private entrance, holiday rental in Bridgeport

Large Studio by the Beach w/private entrance

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fantastic Oceanfront Home ~ Rooftop Deck ~ Outstanding Location!, holiday rental in Bridgeport
Fantastic Oceanfront Home ~ Rooftop Deck ~ Outstanding Location!, holiday rental in Bridgeport
Fantastic Oceanfront Home ~ Rooftop Deck ~ Outstanding Location!, holiday rental in Bridgeport

Fantastic Oceanfront Home ~ Rooftop Deck ~ Outstanding Location!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Lovely River view property , holiday rental in Bridgeport
Lovely River view property , holiday rental in Bridgeport
Lovely River view property , holiday rental in Bridgeport

Lovely River view property

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Comtemporary 1Bdr w/ Queen Bed + Free Wifi, holiday rental in Bridgeport
Comtemporary 1Bdr w/ Queen Bed + Free Wifi, holiday rental in Bridgeport
Comtemporary 1Bdr w/ Queen Bed + Free Wifi, holiday rental in Bridgeport

Comtemporary 1Bdr w/ Queen Bed + Free Wifi

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Lake side retreat with wow views from most rooms, holiday rental in Bridgeport
Lake side retreat with wow views from most rooms, holiday rental in Bridgeport
Lake side retreat with wow views from most rooms, holiday rental in Bridgeport

Lake side retreat with wow views from most rooms

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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My little place, holiday rental in Bridgeport
My little place, holiday rental in Bridgeport
My little place, holiday rental in Bridgeport

My little place

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful Connecticut Abode, close to park & beach, holiday rental in Bridgeport
Beautiful Connecticut Abode, close to park & beach, holiday rental in Bridgeport
Beautiful Connecticut Abode, close to park & beach, holiday rental in Bridgeport

Beautiful Connecticut Abode, close to park & beach

Holiday Rental House
0 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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