Bridgeport Vacation Homes

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Our top choices for Bridgeport holiday homes

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

1. Elite room stay

Bridgeport

HK$2,573 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Brooklawn - St. Vincent

Alma B.

HK$1,998 total

includes taxes & fees

3 Nov - 4 Nov

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

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

North End

David K.

HK$9,808 total

includes taxes & fees

3 Nov - 4 Nov

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

4. Beechmont - Perfect for Family Retreat!

North End

HK$8,389 total

includes taxes & fees

3 Nov - 4 Nov

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

5. Cozy 1-bedroom house in welcoming Bridgeport

Bridgeport

HK$3,591 total

includes taxes & fees

3 Nov - 4 Nov

A swimming pool at night with blue lighting.

6. Business or Weekend escape

Stratford

Kimberly

HK$1,132 total

includes taxes & fees

4 Nov - 5 Nov

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

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

Fairfield

Kim G.

HK$4,289 total

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a black oven.

8. Renovated Beachside Retreat

Milford

Michelle D.

HK$3,398 total

includes taxes & fees

5 Nov - 6 Nov

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

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

Fairfield

Tara C.

HK$4,645 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Tunxis Hill

Emily K.

HK$6,039 total

includes taxes & fees

30 Nov - 1 Dec

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

11. 4 Mi to Beach & Dtwn! Charming Fairfield Home

Tunxis Hill

Raelyn O.

HK$6,936 total

includes taxes & fees

3 Nov - 4 Nov

A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

12. Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Shelton

HK$3,526 total

includes taxes & fees

3 Nov - 4 Nov

A living room with a staircase, a sofa, a coffee table, and a TV.

13. Loft •Pool • Gym • Free Parking • Near Yale

Orange

Ali B.

HK$1,858 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Historic District

Melissa H.

HK$5,015 total

includes taxes & fees

4 Nov - 5 Nov

A living room with a dark grey sofa, a wooden coffee table with a vase of white flowers, a patterned rug, and a ceiling fan.

15. Cozy East Haven Home • Near Beach & Yale

Momauguin

Sarah S.

HK$1,176 total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

16. Gilded Age Luxury Surrounded by Nature

Cranbury

HK$4,315 total

includes taxes & fees

3 Nov - 4 Nov

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

17. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Fair Haven

Jamie S.

HK$1,721 total

includes taxes & fees

9 Nov - 10 Nov

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

18. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Fair Haven

Wallace R.

HK$2,300 total

includes taxes & fees

3 Nov - 4 Nov

A living room with a sofa, a coffee table, a TV, and a lamp.

19. Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

Newhallville

HK$3,092 total

includes taxes & fees

3 Nov - 4 Nov

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

20. Coastal Landing Stay

East Shore

HK$3,788 total

includes taxes & fees

15 Nov - 16 Nov

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Top Bridgeport Hotel Reviews

New Haven Hotel

10/10 Excellent

"Very convenient"

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