Bridgeport Vacation Homes

Bridgeport Vacation Homes
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Our top choices for Bridgeport holiday homes

A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

A spacious living room with a large window, a ceiling fan, a grey sofa, and a coffee table.

A residential street with a house featuring a stone pathway, a white railing, and a clear sky.

A house with a stone facade, a porch with steps, and a wooden ceiling.

1. Centric property close to all the great things in the city

Centric property close to all the great things in the city

Brooklawn - St. Vincent

6.6 out of 10, (17 reviews)

6.6/10

(17 reviews)

"This rental was great accommodation"

Alma B.

The price is HK$1,235

HK$1,235

HK$2,083 total

includes taxes & fees

14 Sept - 15 Sept

Centric property close to all the great things in the city

A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

A bedroom with a bed, a wooden nightstand, a door, and a mirror.

A kitchen with wooden cabinets, a marble countertop, a gas stove, a microwave, and a stainless steel refrigerator.

A shower with beige tiles, a showerhead, and a drain. There are four bottles of shampoo and conditioner on the wall.

2. Elite room stay

Elite room stay

Bridgeport

The price is HK$1,623

HK$1,623

HK$2,674 total

includes taxes & fees

14 Sept - 15 Sept

Elite room stay

A two-story house with a porch, stone steps, and a variety of plants.

A two-story house with a gabled roof, a front porch, and a stone foundation.

A wooden staircase with a chandelier, leading to a room with a large window and a painting on the wall.

A living room with a beige sectional sofa, a patterned rug, and a door leading to an outdoor area.

3. Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

North End

8.8 out of 10, Excellent, (10 reviews)

8.8/10

Excellent

(10 reviews)

"Plenty of bedrooms and space for the family. Very prompt communication with host."

David K.

The price is HK$4,905

HK$4,905

HK$9,770 total

includes taxes & fees

14 Sept - 15 Sept

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

A spacious living room with a patterned armchair, a glass coffee table, and a floral arrangement. A staircase with wooden railings leads to another room.

A living room with a fireplace, wooden beams, a sofa, and a patterned armchair.

4. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5.0 star property

North End

The price is HK$7,561

HK$7,561

HK$11,440 total

includes taxes & fees

13 Sept - 14 Sept

Beechmont - Perfect for Family Retreat!

A bedroom with two beds, a wooden dresser, and a mirror.

A kitchen with dark wood cabinets, a stainless steel refrigerator, a stove, and a white countertop.

A kitchen with a central island, wooden cabinets, a refrigerator, and a dining area with a sofa.

A bedroom with a wooden bed, a dresser, a mirror, and a ceiling light.

5. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport

Bridgeport

The price is HK$2,414

HK$2,414

HK$3,738 total

includes taxes & fees

13 Sept - 14 Sept

Cozy 1-bedroom house in welcoming Bridgeport

A swimming pool at night with blue lighting.

A grey sofa against a brick wall, a bed with white bedding, and a tiled floor with a geometric pattern.

A kitchen area with a black refrigerator, a blue microwave, a coffee maker, and a small table with cereal boxes and a glass.

A room with a bed, a sofa, a dining table with chairs, and a small desk with a keyboard and mouse.

6. Business or Weekend escape

Business or Weekend escape

Stratford

9.2 out of 10, Wonderful, (59 reviews)

9.2/10

Wonderful

(59 reviews)

"Definitely clean - good place for an overnight stay."

Kimberly

The price is HK$706

HK$706

HK$1,194 total

includes taxes & fees

22 Sept - 23 Sept

Business or Weekend escape

A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

A wooden chessboard on a round table with a checkered pattern, set against a backdrop of a living room with a sofa and a small side table.

A staircase with white balusters, a wicker chair, a lamp, and a television mounted on the wall.

A modern living room with a large sofa, a fireplace, and a television.

7. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Fairfield

10.0 out of 10, Exceptional, (39 reviews)

10/10

Exceptional

(39 reviews)

"Great accommodations and perfect location for us. "

Kim G.

The price is HK$2,047

HK$2,047

HK$5,033 total

includes taxes & fees

5 Oct - 6 Oct

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

A modern living room with a white sofa, a round coffee table, and a fireplace.

A two-story house with a front porch, a brick pathway leading to the door, and a small garden with flowers.

A living room with a fireplace, a television, a large window, and two sofas.

8. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Fairfield

10.0 out of 10, Exceptional, (18 reviews)

10/10

Exceptional

(18 reviews)

"Place was very clean . Communication between owner and us was excellent."

gail s.

The price is HK$2,023

HK$2,023

HK$4,826 total

includes taxes & fees

30 Sept - 1 Oct

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

A backyard with a wooden fence, a fire pit, and three Adirondack chairs.

A modern kitchen with white cabinetry, stainless steel appliances, and a large window with a view.

A dining area with a long table, blue upholstered chairs, a bench, and a blue cabinet with a pot on top.

9. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home

Tunxis Hill

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."

Raelyn O.

The price is HK$3,003

HK$3,003

HK$5,682 total

includes taxes & fees

22 Sept - 23 Sept

4 Mi to Beach & Dtwn! Charming Fairfield Home

A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

A modern hotel room with a bed, a desk, a chair, a television, and a door leading to a balcony.

A modern kitchen with a wooden island, white cabinetry, and a large painting above the island.

10. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Tunxis Hill

9.4 out of 10, Exceptional, (20 reviews)

9.4/10

Exceptional

(20 reviews)

"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "

Emily K.

The price is HK$3,680

HK$3,680

HK$7,004 total

includes taxes & fees

16 Sept - 17 Sept

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

A bedroom with two beds, a nightstand with a lamp, a framed picture on the wall, and a window with curtains.

A kitchen with white cabinets, a stainless steel stove, a microwave, and a toaster.

A room with a round table, a framed botanical print on the wall, a chair with a cushion, and a door with a doormat.

A dining room with a wooden table, four chairs, a chandelier, and a mirror.

11. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature

Cranbury

The price is HK$1,835

HK$1,835

HK$3,349 total

includes taxes & fees

13 Sept - 14 Sept

Gilded Age Luxury Surrounded by Nature

A single-story house with a patio area, a chimney, and a garage.

A compact kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and a sink.

A bedroom with a bed, a ceiling fan, a window with curtains, a nightstand, and a mirror.

A living room with a sofa, a coffee table, a potted plant, and artwork on the wall.

12. Peaceful Private Stay in Shared Home Near Yale

Peaceful Private Stay in Shared Home Near Yale

West New Haven

6.0 out of 10, (2 reviews)

6.0/10

(2 reviews)

"Never sent check in information. Had to report them and get refund"

Kimberleigh M.

The price is HK$1,270

HK$1,270

HK$1,633 total

includes taxes & fees

19 Sept - 20 Sept

Peaceful Private Stay in Shared Home Near Yale

A dining area with a table, chairs, a refrigerator, and wall-mounted lights.

A bedroom with a bed, a nightstand, a chair, and a window with curtains.

A two-story house with a front porch, a wooden staircase, and a white door.

A compact kitchen with a stove, sink, and refrigerator. There are framed motivational phrases on the wall.

13. Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

Fair Haven

5.6 out of 10, (4 reviews)

5.6/10

(4 reviews)

"Blankets where itchy and smelled dirty small room when whole house was listed"

Isabella R.

The price is HK$729

HK$729

HK$996 total

includes taxes & fees

14 Sept - 15 Sept

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

A modern living room with a fireplace, a television, and a dining area with chairs and a table.

A dining area with a table and chairs, a vase with flowers, and a fireplace in the background.

A bedroom with a white bed, two bedside tables, a chandelier, and two windows.

A wooden deck with a hanging chair and a barbecue grill.

14. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Historic District

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."

Melissa H.

The price is HK$2,917

HK$2,917

HK$6,228 total

includes taxes & fees

13 Oct - 14 Oct

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

A marina with multiple docks and boats, surrounded by residential buildings and greenery.

A dining area with a white table and chairs, beige walls, and wooden flooring.

A two-story building with a brick base and white upper floors, a front porch, and a staircase leading to the second floor.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a gas stove, and a sink.

15. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Fair Haven

7.6 out of 10, Good, (5 reviews)

7.6/10

Good

(5 reviews)

"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"

Jamie S.

The price is HK$910

HK$910

HK$1,799 total

includes taxes & fees

14 Sept - 15 Sept

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

A room with a large window overlooking a coastal view, a beige sofa, and a small table with books and a vase.

A hallway with a glass door leading to a balcony with a view of the sky and a distant landscape.

A coastal walkway with a metal railing, a clear sky, and houses in the background.

A coastal town with a stone seawall, houses along the beach, and a clear view of the water.

16. Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach

East Shore

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"Great stay! Would definitely stay again! "

Frankie O.

The price is HK$2,294

HK$2,294

HK$4,905 total

includes taxes & fees

14 Sept - 15 Sept

Clear LI Sound waterview, Wedding pics, Yale&Beach

A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

A modern kitchen with wooden cabinets, a central island, and a dining area with two chairs.

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with stools.

A bedroom with a bed, two nightstands, a window with blinds, and two framed pictures on the wall.

17. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside

9.8 out of 10, Exceptional, (19 reviews)

9.8/10

Exceptional

(19 reviews)

"Very nice location, easy check in and check out. Also very comfortable."

Leslie S.

The price is HK$1,510

HK$1,510

HK$2,952 total

includes taxes & fees

15 Sept - 16 Sept

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

A spacious living room with a grey sectional sofa, a small ottoman, and a large window with a view.

A modern kitchen with wooden cabinets, a black refrigerator, a microwave, and a stove. There is a dining table with chairs and a potted plant.

A spacious bedroom with a large bed, three windows with blinds, and a light-colored wooden floor.

18. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Fair Haven

9.6 out of 10, Exceptional, (15 reviews)

9.6/10

Exceptional

(15 reviews)

"A cozy pet and family-friendly property. Very spacious."

Wallace R.

The price is HK$1,404

HK$1,404

HK$2,610 total

includes taxes & fees

29 Sept - 30 Sept

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

A modern kitchen with white cabinetry, a central island with stools, pendant lighting, and a view to an outdoor area.

A modern living room with a white brick fireplace, white sofas, a coffee table, and a flat-screen TV mounted above the fireplace.

A modern living room with a white sofa, a glass coffee table, and a bookshelf. There are framed pictures on the wall and a door leading to another room.

A modern living room with a glass coffee table, white sofa, and a fireplace.

19. Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

East Shore

8.8 out of 10, Excellent, (5 reviews)

8.8/10

Excellent

(5 reviews)

"Fantastic place, amazing hosts, 100% recommend! "

Zach P.

The price is HK$2,104

HK$2,104

HK$5,676 total

includes taxes & fees

15 Sept - 16 Sept

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

A modern kitchen with a stainless steel refrigerator, wooden beams, a dining area with a table and chairs, and a large window with blinds.

A spacious living area with a wooden dining table, white chairs, a bench, and a sofa.

A hallway with a wooden-framed mirror, a white door, and a light switch on the wall.

20. Coastal Landing Stay

Coastal Landing Stay

East Shore

The price is HK$1,600

HK$1,600

HK$3,952 total

includes taxes & fees

13 Sept - 14 Sept

Coastal Landing Stay

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Bridgeport Hotel Reviews

La Quinta Inn & Suites by Wyndham Stamford / New York City

8/10 Good

"Parking lot good. breakfast was 👍"

Peter 4-night trip

Posted 3 hours ago

La Quinta Inn & Suites by Wyndham Stamford / New York City

Wyndham Southbury

10/10 Excellent

"There’s a restaurant in a bar inside great service, staff, friendly room, spacious and clean fairly upgraded"

Taneshia 1-night trip

Posted 7 hours ago

Wyndham Southbury

Danfords Hotel and Marina

10/10 Excellent

"Amazing room size and very quiet. Loved it here. Will stay again,"

martha 3-night trip

Posted 10 hours ago

Danfords Hotel and Marina

Hyatt Place Milford / New Haven

10/10 Excellent

"Great customer service. Nice, clean room."

Michael 1-night trip

Posted 11 hours ago

Hyatt Place Milford / New Haven

Amsterdam Hotel

8/10 Good

"Very good value. The gym is a little primitive but functional. Breakfast is basic. The staff was very friendly. Free parking and everything was clean and neat"

david 1-night trip

Posted 2 days ago

Amsterdam Hotel

Best Western Executive Hotel Of New Haven - West Haven

8/10 Good

"Good"

SHEHLA 4-night trip

Posted 2 days ago

Best Western Executive Hotel Of New Haven - West Haven

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