Bridgeport holiday rentals

We found 1,286 holiday rentals — enter your dates for availability
Discover a selection of 35 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:6 Nov - 13 Nov

Living area
Pool
Living area
Interior
Exceptional
(8 reviews)

Nature & Luxury @Lavender Lake Est (Kosher optional)

Roxbury

8% off
AU$13,440
for 7 nights, 1 home
AU$1,920 per night
includes taxes & fees
Nature & Luxury @Lavender Lake Est (Kosher optional)
Living room
Front of house
Kitchen
Kitchen
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
AU$12,450
for 7 nights, 1 home
AU$1,779 per night
includes taxes & fees
Fairfield Beach Modern Colonial
All season jacuzzi
18' x 36' heated pool.
2nd Floor view from Primary I
Four season six person jacuzzi set at 104 degrees!
Exceptional
(55 reviews)

Litchfield County Four Season Country Paradise

Roxbury

8% off
AU$11,682
for 7 nights, 1 home
AU$1,669 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
Sunset
Sunset at Lookout Point
Lookout in Fall
Lookout in Summer
Exceptional
(9 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

8% off
AU$18,091
for 7 nights, 1 home
AU$2,584 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
Outdoor dining
Interior
Dining
Private kitchen
Exceptional
(20 reviews)

Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups

Brookfield

17% off
AU$17,910
for 7 nights, 1 home
AU$2,559 per night
includes taxes & fees
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups
Interior
Terrace/patio
Living area
Living area
Exceptional
(5 reviews)

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

Trumbull

8% off
AU$14,552
for 7 nights, 1 home
AU$2,079 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Living area
Beach
Living area
Living area
Exceptional
(9 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

8% off
AU$4,010
for 7 nights, 1 cottage
AU$573 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Dining
Pool
Pool
Pool
Exceptional
(5 reviews)

2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC

Fairfield

8% off
AU$26,241
for 7 nights, 1 home
AU$3,749 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Exterior
Exterior
Exterior
Outdoor dining
Exceptional
(16 reviews)

Spacious Modern Beach House, perfect for families

Branford

8% off
AU$6,997
for 7 nights, 1 home
AU$1,000 per night
includes taxes & fees
Spacious Modern Beach House, perfect for families
Exterior
Living area
Property grounds
Beach
Exceptional
(5 reviews)

On the Water Spacious Comfortable Historic Home

West Haven

8% off
AU$9,768
for 7 nights, 1 home
AU$1,395 per night
includes taxes & fees
On the Water Spacious Comfortable Historic Home
Living area
Pool
Exterior
Bathroom
Exceptional
(7 reviews)

Private Home - Pool and Close to CT Shoreline Beaches

North Branford

17% off
AU$13,995
for 7 nights, 1 home
AU$1,999 per night
includes taxes & fees
Private Home - Pool and Close to CT Shoreline Beaches
Plenty of counter space in this well equipped kitchen.
good morning...
sunrise in winter...
(new photo 6/25/2011)
View from the master bedroom.
Exceptional
(52 reviews)

Beautiful Waterfront Beach House for Family Vacations

Branford

8% off
AU$8,667
for 7 nights, 1 home
AU$1,238 per night
includes taxes & fees
Beautiful Waterfront Beach House for Family Vacations
Interior
Terrace/patio
Living area
Outdoor dining
Exceptional
(30 reviews)

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

Danbury

8% off
AU$11,050
for 7 nights, 1 home
AU$1,579 per night
includes taxes & fees
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Bedroom 1
Exterior
Terrace/patio
Outdoor dining
Exceptional
(6 reviews)

Silver Sands Beach Getaway

Milford

16% off
AU$4,416
for 7 nights, 1 home
AU$631 per night
includes taxes & fees
Silver Sands Beach Getaway
Living Room
Exterior of House with AMPLE Parking
The Kitchen
1 King Size Bed with View of River
Exceptional
(15 reviews)

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

New Haven

8% off
AU$4,290
for 7 nights, 1 home
AU$613 per night
includes taxes & fees
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Outdoor dining
Exterior
Terrace/patio
Terrace/patio
Exceptional
(18 reviews)

Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury

Southbury

8% off
AU$4,423
for 7 nights, 1 home
AU$632 per night
includes taxes & fees
Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury
Private kitchen
Private kitchen
Private kitchen
Interior
Very good
(9 reviews)

Excellent Home Away From Home

Waterbury

15% off
AU$2,178
for 7 nights, 1 home
AU$311 per night
includes taxes & fees
Excellent Home Away From Home
Front , plenty of parking.
Aerial view
Flat yard,
Exterior
Exceptional
(85 reviews)

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

New Fairfield

8% off
AU$17,776
for 7 nights, 1 home
AU$2,539 per night
includes taxes & fees
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Living area
Room
Bathroom
Private kitchen
Exceptional
(21 reviews)

Beautiful Private Studio Apartment!

Ridge

7% off
AU$1,669
for 7 nights, 1 apartment
AU$238 per night
includes taxes & fees
Beautiful Private Studio Apartment!
Room
Exterior
Room
Living area
Exceptional
(6 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
AU$8,967
for 7 nights, 1 home
AU$1,281 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Dining
Room
Bathroom
Room
Exceptional
(5 reviews)

Cozy studio with 1 bedroom in peaceful Stratford retreat

Stratford

8% off
AU$741
for 7 nights, 1 apartment
AU$106 per night
includes taxes & fees
Cozy studio with 1 bedroom in peaceful Stratford retreat
Room
Pool
Room
Room
Excellent
(35 reviews)

The Jahmtons Guest Room

Ridge

8% off
AU$1,480
for 7 nights, 1 room
AU$211 per night
includes taxes & fees
The Jahmtons Guest Room
view of outside door and bathroom door from kitchen
Port Jeff Harbor
Satterly Landing short walk away
Door to outside, Like the flowers?
Exceptional
(59 reviews)

1856 Trading House w/ walk to water

Mount Sinai

12% off
AU$3,051
for 7 nights, 1 apartment
AU$436 per night
includes taxes & fees
1856 Trading House w/ walk to water
Living area
Room
Interior
Exterior
Exceptional
(20 reviews)

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

Ridge

7% off
AU$2,034
for 7 nights, 1 apartment
AU$291 per night
includes taxes & fees
Comfy, private one Bedroom Apartment with full kitchen, living room, full bath.
  • 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

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)
  • Country Club of Fairfield (5.8 mi / 9.3 km)
  • Grassy Hill Country Club (9.5 mi / 15.2 km)
  • Norwalk Maritime Aquarium (13 mi / 20.9 km)
  • Great River Golf Club (8.5 mi / 13.6 km)
  • Connecticut Golf Club (8.9 mi / 14.3 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)
  • The Coastal Center at Milford Point (5 mi / 8 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 Stayz 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? Stayz 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 Stayz 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 Stayz 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 Stayz. 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 Stayz 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 Stayz.
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 Stayz, 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 Stayz. 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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