Bridgeport holiday homes

We found 1,289 holiday rentals — enter your dates for availability
Discover a selection of 34 homes, 40 apartments and other holiday rentals in Bridgeport that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the amenities that you expect and more, which might include a hot tub and garden. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Bridgeport

Showing deals for:27 Nov - 4 Dec

Living Room
Sunset
Kitchen
Foyer
Exceptional
(9 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

8% off
NZ$21,323
for 7 nights, 1 home
NZ$3,046 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
Kitchen
View of back of house
Front of house
Stairs leading to third floor
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
NZ$14,606
for 7 nights, 1 home
NZ$2,087 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Movie room with 85" 4k screen and surround sound Sonos System
Gorgeous sunsets every night
Private kitchen
18' x 36' heated pool.
Exceptional
(55 reviews)

Litchfield County Four Season Country Paradise

Roxbury

7% off
NZ$16,313
for 7 nights, 1 home
NZ$2,330 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
Property grounds
Terrace/patio
Dining
Pool
Exceptional
(5 reviews)

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Trumbull

8% off
NZ$17,083
for 7 nights, 1 home
NZ$2,440 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Open layout living
Enjoy lounging after a long beach day on the sectional looking out at the water
Exterior
Fully stocked kitchen with stainless steel appliances and breakfast counter
Exceptional
(10 reviews)

Luxury Beach Oasis with Amazing Panoramic Ocean Views

Milford

8% off
NZ$11,402
for 7 nights, 1 home
NZ$1,629 per night
includes taxes & fees
Luxury Beach Oasis with Amazing Panoramic Ocean Views
Interior
Outdoor dining
Dining
Exterior
Exceptional
(5 reviews)

On the Water Spacious Comfortable Historic Home

West Haven

8% off
NZ$11,664
for 7 nights, 1 home
NZ$1,666 per night
includes taxes & fees
On the Water Spacious Comfortable Historic Home
Family room by night with garage doors retracted.
Outdoor dining
Private kitchen
Well stocked eat-in kitchen with stainless appliances.
Exceptional
(120 reviews)

Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct

Danbury

7% off
NZ$7,060
for 7 nights, 1 home
NZ$1,009 per night
includes taxes & fees
Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct
Private kitchen
Living area
Property grounds
Living area
Exceptional
(10 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

8% off
NZ$4,815
for 7 nights, 1 cottage
NZ$688 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Exterior
Interior
Property grounds
Property grounds
Exceptional
(33 reviews)

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury

8% off
NZ$13,495
for 7 nights, 1 home
NZ$1,928 per night
includes taxes & fees
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
main floor, king bed with bathroom, fireplace, slider opens to deck and hot tub.
Flat yard,
Living area
double fridge for extea space
Exceptional
(85 reviews)

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

New Fairfield

8% off
NZ$20,945
for 7 nights, 1 home
NZ$2,992 per night
includes taxes & fees
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Living area
Interior
Living area
Private kitchen
Excellent
(5 reviews)

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

East Haven

7% off
NZ$6,473
for 7 nights, 1 home
NZ$925 per night
includes taxes & fees
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
Exterior detail
Pool
Room
Pool
Excellent
(36 reviews)

The Jahmtons Guest Room

Ridge

8% off
NZ$1,711
for 7 nights, 1 room
NZ$244 per night
includes taxes & fees
The Jahmtons Guest Room
Kitchen
Outdoor dining
Living area
Living area
Exceptional
(7 reviews)

Silver Sands Beach Getaway

Milford

16% off
NZ$5,302
for 7 nights, 1 home
NZ$757 per night
includes taxes & fees
Silver Sands Beach Getaway
(new photo 6/25/2011)
Interior
Home from the water. (Blue house in center of photo)
Living area
Exceptional
(53 reviews)

Beautiful Waterfront Beach House for Family Vacations

Branford

8% off
NZ$10,342
for 7 nights, 1 home
NZ$1,477 per night
includes taxes & fees
Beautiful Waterfront Beach House for Family Vacations
Terrace/patio
Dining
Exterior
Pool
Exceptional
(7 reviews)

Private Home - Pool and Close to CT Shoreline Beaches

North Branford

17% off
NZ$17,700
for 7 nights, 1 home
NZ$2,529 per night
includes taxes & fees
Private Home - Pool and Close to CT Shoreline Beaches
Dining
Living area
Terrace/patio
Interior
Excellent
(27 reviews)

Relaxing Cottage -- Walk to private Beach!

Calverton

7% off
NZ$3,806
for 7 nights, 1 cottage
NZ$544 per night
includes taxes & fees
Relaxing Cottage -- Walk to private Beach!
Outdoor dining
Exterior
Room
Living area
Exceptional
(21 reviews)

Beautiful Private Studio Apartment!

Ridge

7% off
NZ$1,928
for 7 nights, 1 apartment
NZ$275 per night
includes taxes & fees
Beautiful Private Studio Apartment!
Outdoor dining
Exterior
Private kitchen
Room
Exceptional
(21 reviews)

Comfy, private one Bedroom Apartment with full kitchen, living room, full bath.

Ridge

7% off
NZ$2,352
for 7 nights, 1 apartment
NZ$336 per night
includes taxes & fees
Comfy, private one Bedroom Apartment with full kitchen, living room, full bath.
Exterior
Property grounds
Terrace/patio
Private kitchen
Exceptional
(14 reviews)

Cozy cottage with AC and lake access in charming Connecticut suburb.

Watertown

8% off
NZ$2,458
for 7 nights, 1 cottage
NZ$351 per night
includes taxes & fees
Cozy cottage with AC and lake access in charming Connecticut suburb.
Dining Room
Stairwell to Master
Kitchen
Living Room
Excellent
(6 reviews)

Beach Apartment in Woodmont Milford

Milford

8% off
NZ$3,816
for 7 nights, 1 apartment
NZ$545 per night
includes taxes & fees
Beach Apartment in Woodmont Milford
Interior
Interior
Interior
Room
Exceptional
(31 reviews)

1856 Trading House close to water

Mount Sinai

12% off
NZ$3,570
for 7 nights, 1 apartment
NZ$510 per night
includes taxes & fees
1856 Trading House close to water
Living area
Your view everyday!
Interior
Living area
Exceptional
(46 reviews)

#2 Beautiful Milford Beach Right Across Street - Charles Island/Silver Sands Pk

Milford

8% off
NZ$3,960
for 7 nights, 1 apartment
NZ$566 per night
includes taxes & fees
#2 Beautiful Milford Beach Right Across Street - Charles Island/Silver Sands Pk
Kitchen
View of the Pond
Bathroom
Living Room
Exceptional
(7 reviews)

Private Apartment in Southbury 101

Southbury

8% off
NZ$2,289
for 7 nights, 1 apartment
NZ$327 per night
includes taxes & fees
Private Apartment in Southbury 101
Terrace/patio
Private kitchen
Exterior
Living area
Exceptional
(57 reviews)

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Centereach

8% off
NZ$7,315
for 7 nights, 1 home
NZ$1,045 per night
includes taxes & fees
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Bridgeport

  • Beautiful Riverfront: Bridgeport's scenic riverfront offers picturesque views and a perfect spot for leisurely walks along the water.
  • Urban Parks and Beaches: Enjoy various parks and sandy beaches that provide ample opportunities for outdoor activities and relaxation.
  • Cultural Heritage: Immerse yourself in local history at the Bridgeport history centre, showcasing the city's rich past and cultural significance.
  • Distinctive Landmarks: Explore historic landmarks that reflect Bridgeport's unique architectural heritage and charm.
  • Vibrant Community Life: Experience friendly neighbourhoods filled with local art, dining, and events that bring the community together.

Top attractions near Bridgeport

Bridgeport, Connecticut offers a vibrant city experience perfect for families and outdoor enthusiasts alike. Enjoy its urban parks, sandy beaches, and national state parks, and immerse yourself in local culture at the Bridgeport history centre. The city's unique attractions and activities provide plenty of opportunities for memorable exploration and relaxation, making it an ideal destination for a diverse holiday experience.

  • Walnut Beach: This lovely beach offers a relaxing getaway with soft sands and refreshing waves, perfect for sunbathing, picnicking, or enjoying a leisurely stroll along the shore.
  • Milford Green: A charming urban park that serves as a community hub, featuring open green spaces, playgrounds, and picnic areas, making it ideal for family outings and outdoor activities.
  • Lockwood-Mathews Mansion: A stunning historic house showcasing exquisite architecture and rich cultural heritage, offering guided tours that delve into its fascinating history and elegant interiors.

Things to do recommended for couples

Discover the charm of Bridgeport with a romantic stroll along the waterfront at Seaside Park or enjoy a sunset cruise on the Black Rock Harbour. Don't forget to visit the eclectic local eateries for a delightful dining experience together.

Things to do recommended for families

Families visiting Bridgeport can enjoy a fun-filled day at the Beardsley Zoo, home to various animals and engaging exhibits. Additionally, a visit to the Discovery Museum offers interactive science exhibits and planetarium shows that will captivate both young and old alike.

Things to do recommended for groups

Experience the thrill of the Adventure Park at Discovery Museum, where your group can tackle an exciting zipline and ropes course. Enjoy the outdoor vibes and create lasting memories as you navigate through the treetops together in Bridgeport.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Bridgeport

When planning your trip—whether you're travelling with a group, family, pets, or seeking extended stays—it's important to prioritise your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Bridgeport with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or an outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Bridgeport with young kids: Travelling with young children can present its challenges. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is a wise choice.
  • Taking your pets with you to Bridgeport: Some families wouldn’t consider a trip complete without their furry companion. If you’re one of them, take a look at Vrbo properties that welcome pets. Many of these pet-friendly homes come with feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Bridgeport: If you’re after holiday rentals that offer special rates for month-long stays, you’ve come to the right spot. Use the appropriate filter to effortlessly locate and save on monthly rentals, and don’t forget to include options like parking, a well-equipped kitchen, or a private pool in your search.

Where to stay near Bridgeport

Bridgeport offers a delightful blend of urban charm and outdoor adventures, perfect for family and romantic escapes. Explore its vibrant riverfront, historic landmarks, and bustling city life, where local art and friendly neighbourhoods invite you to immerse in the essential bridgeport experience. Discover scenic parks and cultural treasures that truly capture the spirit of this Connecticut gem.

  • Fairfield: Located 8km from Bridgeport, Fairfield offers a delightful blend of city life and outdoor adventures. Visitors can immerse themselves in the local culture, with attractions like a modern college university and beautiful family beaches. The city is perfect for those looking to enjoy a round of golf or explore recreational areas, making it an ideal spot for families and culture enthusiasts alike. Whether you’re strolling along the beach or engaging in educational experiences, Fairfield promises a memorable outing.
  • Milford: Situated 13km from Bridgeport, Milford is renowned for its picturesque scenery and outdoor activities, making it a family-friendly destination. With its stunning beaches and historic college university, visitors can enjoy a day of exploration or relaxation by the water. The city features various recreational areas and is great for those who appreciate natural beauty and family-oriented experiences. Whether you're picnicking on the beach or exploring walking trails, Milford offers a refreshing escape.
  • Norwalk: Just 19km from Bridgeport, Norwalk is a vibrant city that caters to families and outdoor enthusiasts. Known for its shopping areas and educational institutions, Norwalk also boasts beautiful beaches perfect for a relaxing day out. Visitors can enjoy a variety of activities, including golfing and exploring local attractions, all while soaking in the city’s lively atmosphere. With its charming blend of urban and natural experiences, Norwalk is a must-visit on your holiday itinerary.

Best time to go to Bridgeport

If you're planning a trip to Bridgeport, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.8°F (-0.1°C)Light RainMostly SunnySlightly Low
February32.9°F (0.5°C)Light RainMostly SunnyAverage
March39.0°F (3.9°C)Light RainMostly SunnyAverage
April48.9°F (9.4°C)Light RainMostly SunnyAverage
May58.8°F (14.9°C)Light RainMostly SunnyAverage
June67.6°F (19.8°C)Light RainMostly SunnySlightly High
July74.8°F (23.8°C)Light RainMostly SunnySlightly High
August73.9°F (23.3°C)Light RainMostly SunnyAverage
September67.5°F (19.7°C)Light RainMostly SunnySlightly High
October57.4°F (14.1°C)Light RainMostly SunnyAverage
November46.2°F (7.9°C)Light RainMostly SunnySlightly Low
December38.3°F (3.5°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is a breeze

Looking to get a great deal on your next getaway? Being flexible with your travel dates can really make a difference, as prices often fluctuate. You could also enjoy considerable savings by booking a longer stay. To find a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly space where you can easily create new trips, resume planning, or review and organise your travel arrangements. Here, you'll find properties you’ve either saved or booked, neatly categorised under Potential, Upcoming, or Current Trips. To get started with Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Delight in the beachside landscape of Bridgeport

Come and experience Bridgeport and its live music, theatre scene and festivals. This walkable city is known for its zoo, baseball games and beaches. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Bridgeport

Are you hoping to discover attractions to see while you're in town? Venture out of your holiday home and check out everything that Bridgeport has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Beardsley Zoo (1.8 mi / 3 km)
  • Great River Golf Club (8.5 mi / 13.6 km)
  • Norwalk Maritime Aquarium (13 mi / 20.9 km)
  • Country Club of Fairfield (5.8 mi / 9.3 km)
  • Connecticut Golf Club (8.9 mi / 14.3 km)
  • Grassy Hill Country Club (9.5 mi / 15.2 km)

Exploring the natural landscape of Bridgeport

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Bridgeport is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Seaside Park (1.7 mi / 2.8 km)
  • Seaside Beach (2 mi / 3.2 km)
  • Jennings Beach (3.8 mi / 6.1 km)
  • Penfield Beach (4.4 mi / 7 km)
  • Short Beach (4.7 mi / 7.5 km)
  • Lordship Beach (5.1 mi / 8.3 km)

Transport options to and around Bridgeport

Fly into Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), the closest airport, located 3.7 mi (6 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is 16.8 mi (27.1 km) away.

If you're travelling by train, the main station is Bridgeport Station.

Frequently asked questions

What is the best area to stay in Bridgeport when booking a holiday home?
One of the most desired neighbourhoods to book a holiday home in Bridgeport is Black Rock Historic District. Discover your dream stay on Bookabach and explore this area like a local.
What is the most popular type of holiday home accommodation in Bridgeport?
The most desirable types of holiday homes in Bridgeport are houses. Searching for something different? Bookabach has numerous options to match our guests' unique needs, so you'll see properties in all sizes and shapes. The perfect fit is waiting for you — discover yours today.
How much does it cost to rent a holiday home in Bridgeport?
Property type, length of stay and season are some of the conditions that can influence the price of a holiday home. Simply add your travel dates to find your ideal match. From homey country cottages to sprawling villas, all Bookabach holiday homes offer amazing value.
How much does it cost to rent a beach house in Bridgeport?
The average price for a holiday home near the beach in Bridgeport will depend on when you're going and the size and type of property you're searching for. You can quickly and easily find prices on Bookabach by entering your destination and preferred travel dates. Then use the handy filter tool to choose the number of bedrooms and amenities that you require, like air conditioning, a pool and WiFi.
Are there pet-friendly holiday homes in Bridgeport?
Pack a travel bag for your beloved pooch because Bridgeport has 22 properties that roll out the welcome mat to doggie guests. Let your furriest pal get in on the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your dates and destination, then check our "Pets allowed" filter box.
What are popular home amenities in Bridgeport?
When it comes to home amenities that people prefer in Bridgeport, a fireplace, a barbecue grill and a garden rank the highest. With Bookabach holiday homes, there are choices to match your taste and style, whether you're going on a holiday with friends, relatives or even pets.
Are there large group holiday homes in Bridgeport?
Bridgeport has two holiday homes that can host 10 or more guests. These properties come with the space you need to share good times with your nearest and dearest.
Are there holiday homes in Bridgeport that welcome kids?
Gather the whole crew for fun-filled adventures in Bridgeport at one of our 22 family-friendly properties. These stays feature amenities that are ideally suited to trips with the little ones, including laundries, extra bedrooms and swimming pools. Simply click on the "Properties good for families" filter and pick out your favourite.
What are the top attractions for families in Bridgeport?
There are tons of amazing things to do and see with the family in Bridgeport, such as:
  • Jennings Beach
  • Beardsley Zoo
  • Seaside Beach
Are there one-bedroom holiday homes in Bridgeport?
Bridgeport has three one-bedroom homes available. Usually situated in well-regarded areas thanks to their smaller size, a one-bedroom holiday home is great if you're getting away with a buddy or your partner. And with comforts like air conditioning and more privacy than a standard hotel, you'll be able to chill out while sightseeing around this incredible destination.
Can I find two-bedroom holiday homes in Bridgeport?
You can pick from 10 two-bedroom holiday homes in Bridgeport. Settle the kids into the second room or maybe fill it with a couple of your favourite people. There's ample space for whoever's fortunate enough to be coming along.
Are there holiday homes with WiFi in Bridgeport?
Pick from 11 holiday homes with WiFi in Bridgeport. If you want to disconnect from daily life on your break, but still need to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Bridgeport?
You can choose from 15 holiday homes with air conditioning in Bridgeport offering that cooling breeze and extra element of comfort. Enter your dates of travel and then use our filters to help you book properties with air conditioning.
How old do you have to be to rent a holiday home in Bridgeport?
The minimum age requirements can vary across properties on Bookabach, so be sure to look at the rules of the holiday home in Bridgeport you're interested in. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Bridgeport for?
It's really down to the Bridgeport property. To look over a list of options offering extended stays, just enter your dates and number of guests into Bookabach. Look forward to having the property to yourself, along with amenities such as air conditioning, a fully-equipped kitchen and a backyard where the kids can play. Keep your eyes open for any long-term stays that offer discounted weekly or monthly prices.

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