Bridgeport holiday rentals

We found 1,287 holiday rentals — enter your dates for availability
Discover a selection of 33 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:25 Dec - 1 Jan

Private kitchen
Living area
Balcony
Dining
Exceptional
(8 reviews)

Nature & Luxury @Lavender Lake Est (Kosher optional)

Roxbury

8% off
AU$12,360
for 7 nights, 1 home
AU$1,766 per night
includes taxes & fees
Nature & Luxury @Lavender Lake Est (Kosher optional)
Kitchen
Sunset
Living Room
Foyer
Exceptional
(9 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

5% off
AU$18,661
for 7 nights, 1 home
AU$2,666 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
Cozy seating area with dual water views
You will love the Center Island cooktop open kitchen & beautiful water views
Experience Stunning panoramic Water Views from every area of the home
Sunsets are simply breath taking over the water
Exceptional
(74 reviews)

Waterfront Retreat, Private Beach + Hot Tub Sunsets

Branford

15% off
AU$14,896
for 7 nights, 1 home
AU$2,128 per night
includes taxes & fees
Waterfront Retreat, Private Beach + Hot Tub Sunsets
Private kitchen
Gorgeous sunsets every night
18' x 36' heated pool.
Movie room with 85" 4k screen and surround sound Sonos System
Exceptional
(56 reviews)

Litchfield County Four Season Country Paradise

Roxbury

8% off
AU$13,175
for 7 nights, 1 home
AU$1,882 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
Living room
View of back of house
Stairs leading to third floor
Kitchen
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
AU$12,290
for 7 nights, 1 home
AU$1,756 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Private kitchen
Outdoor dining
Well stocked eat-in kitchen with stainless appliances.
Family room by night with garage doors retracted.
Exceptional
(122 reviews)

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

Danbury

8% off
AU$5,852
for 7 nights, 1 home
AU$836 per night
includes taxes & fees
Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct
Large comfortable sectional with a 70" smart tv
Enjoy lounging after a long beach day on the sectional looking out at the water
Open layout living
Fully stocked kitchen with stainless steel appliances and breakfast counter
Exceptional
(10 reviews)

Luxury Beach Oasis with Amazing Panoramic Ocean Views

Milford

8% off
AU$10,395
for 7 nights, 1 home
AU$1,485 per night
includes taxes & fees
Luxury Beach Oasis with Amazing Panoramic Ocean Views
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
AU$14,365
for 7 nights, 1 home
AU$2,052 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Property grounds
Living area
Living area
Private kitchen
Exceptional
(11 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

8% off
AU$4,028
for 7 nights, 1 cottage
AU$575 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Living area
Living area
Room
Terrace/patio
Exceptional
(5 reviews)

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

Fairfield

8% off
AU$30,062
for 7 nights, 1 home
AU$4,295 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
View from property
Flat yard,
Living area
double fridge for extea space
Exceptional
(87 reviews)

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

New Fairfield

8% off
AU$18,804
for 7 nights, 1 home
AU$2,686 per night
includes taxes & fees
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Front of Cottage 2024
small, covered front porch on cottage
Interior
Lovely rolling 8 Acre farmland is shared with the main house
Exceptional
(9 reviews)

Clean & Bright 2 Bedroom Cottage shares 8 Acres

Southbury

16% off
AU$3,598
for 7 nights, 1 cottage
AU$514 per night
includes taxes & fees
Clean & Bright 2 Bedroom Cottage shares 8 Acres
Property grounds
Interior
Property grounds
Private kitchen
Exceptional
(35 reviews)

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

Danbury

8% off
AU$10,908
for 7 nights, 1 home
AU$1,558 per night
includes taxes & fees
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
(new photo 6/25/2011)
Interior
Home from the water. (Blue house in center of photo)
Living area
Exceptional
(54 reviews)

Beautiful Waterfront Beach House for Family Vacations

Branford

8% off
AU$8,555
for 7 nights, 1 home
AU$1,222 per night
includes taxes & fees
Beautiful Waterfront Beach House for Family Vacations
Living area
Outdoor dining
Kitchen
Living area
Exceptional
(8 reviews)

Silver Sands Beach Getaway

Milford

16% off
AU$4,436
for 7 nights, 1 home
AU$634 per night
includes taxes & fees
Silver Sands Beach Getaway
Living Room
Lake View
The Kitchen
1 King Size Bed with View of River
Exceptional
(16 reviews)

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

New Haven

8% off
AU$3,384
for 7 nights, 1 home
AU$483 per night
includes taxes & fees
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Room
Pool
Room
Exterior detail
Excellent
(36 reviews)

The Jahmtons Guest Room

Ridge

8% off
AU$1,461
for 7 nights, 1 room
AU$209 per night
includes taxes & fees
The Jahmtons Guest Room
Private kitchen
Private kitchen
Room
Dining
Very good
(9 reviews)

Excellent Home Away From Home

Waterbury

15% off
AU$2,150
for 7 nights, 1 home
AU$307 per night
includes taxes & fees
Excellent Home Away From Home
Dining
Living area
Interior
Private kitchen
Excellent
(27 reviews)

Relaxing Cottage -- Walk to private Beach!

Calverton

7% off
AU$3,248
for 7 nights, 1 cottage
AU$464 per night
includes taxes & fees
Relaxing Cottage -- Walk to private Beach!
Pool
Dining
Terrace/patio
Private kitchen
Exceptional
(7 reviews)

Private Home - Pool and Close to CT Shoreline Beaches

North Branford

17% off
AU$14,614
for 7 nights, 1 home
AU$2,088 per night
includes taxes & fees
Private Home - Pool and Close to CT Shoreline Beaches
Private kitchen
Property grounds
Living area
Exterior
Exceptional
(15 reviews)

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

Watertown

8% off
AU$2,098
for 7 nights, 1 cottage
AU$300 per night
includes taxes & fees
Cozy cottage with AC and lake access in charming Connecticut suburb.
Interior
Private kitchen
Exterior
Room
Exceptional
(6 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
AU$8,852
for 7 nights, 1 home
AU$1,265 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Dining
Terrace/patio
Exterior
Living area
Exceptional
(47 reviews)

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy

East Haven

17% off
AU$9,272
for 7 nights, 1 home
AU$1,325 per night
includes taxes & fees
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
Living area
Private kitchen
Living area
Terrace/patio
Exceptional
(59 reviews)

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

Centereach

8% off
AU$6,181
for 7 nights, 1 home
AU$883 per night
includes taxes & fees
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

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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)
  • Norwalk Maritime Aquarium (13 mi / 20.9 km)
  • Country Club of Fairfield (5.8 mi / 9.3 km)
  • Great River Golf Club (8.5 mi / 13.6 km)
  • Connecticut Golf Club (8.9 mi / 14.3 km)
  • Yale Golf Course (14.2 mi / 22.9 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)
  • Lake Mohegan (3.5 mi / 5.7 km)
  • Jennings Beach (3.8 mi / 6.1 km)
  • Penfield Beach (4.4 mi / 7 km)
  • Short Beach (4.7 mi / 7.5 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 rental?
When considering a holiday rental in Bridgeport, Connecticut, the Downtown area is often regarded as one of the best choices. This vibrant neighbourhood offers a mix of cultural attractions and convenient amenities, making it ideal for both relaxation and exploration. Here, you'll find the renowned Beardsley Zoo, which showcases a variety of wildlife and is a lovely spot for families and animal lovers alike. The Downtown area is also home to the historic Bijou Theatre, where you can enjoy a range of performances, from live music to film screenings.Additionally, the Seaside Park area is another excellent option, particularly for those who appreciate natural beauty and outdoor activities. This expansive park offers picturesque views of Long Island Sound, along with walking trails and picnic areas, great for a leisurely day outdoors. The area's proximity to the waterfront adds to its charm, allowing for a refreshing coastal experience.While the exact number of properties may vary, both Downtown and Seaside Park typically have a diverse selection of holiday rentals, suiting different tastes and budgets.
Where are the best areas for renting a beach house in Bridgeport?
For renting a beach house in Bridgeport, consider the picturesque area around Seaside Park, which offers a lovely stretch of sandy beach superb for a relaxing getaway. Many properties in this neighbourhood come with amenities such as outdoor decks, BBQ grills, and spacious living areas, ideal for families or groups enjoying a beachside retreat. The proximity to the park provides opportunities for picnicking and outdoor activities, along with easy access to the beach, making it a popular choice for travellers.Further along the coast, the neighbourhood near Pleasure Beach offers a more secluded beach experience. Here, you can find charming cottages and bungalows that often feature private balconies and direct beach access. These rentals may include amenities like fully equipped kitchens and laundry facilities, providing convenience for longer stays. The area is known for its serene atmosphere and stunning views of Long Island Sound, superb for those looking to unwind.Moreover, the nearby Black Rock area provides additional options for beach houses, characterised by a vibrant community and local eateries. Properties here may come with amenities such as fire pits and outdoor seating areas, allowing guests to enjoy the coastal evenings. The proximity to local shops and cafes adds a touch of convenience, making it an ideal location for those wanting both beach access and a taste of local culture.
What is the most popular type of holiday rental accomodation in Bridgeport?
In Bridgeport, apartments are the most prevalent type of holiday rental, with approximately 84 available throughout the city. These apartments are typically located in convenient neighbourhoods, providing easy access to local attractions such as the Beardsley Zoo and the scenic waterfront. Most units feature fully equipped kitchens, comfortable living areas, and amenities like Wi-Fi and laundry facilities, making them ideal for both short and extended stays.In addition to apartments, there are around 69 holiday houses that cater to families or groups seeking more space. These homes often come with multiple bedrooms, outdoor areas, and sometimes even BBQ facilities, superb for gatherings after a day of exploring the area. Additionally, there are several cottages and villas available, offering unique and charming accommodations.
Are there any family house rentals in Bridgeport?
In Bridgeport, Connecticut, there are around 30 family-friendly homes available for rent, making it an excellent choice for those travelling with children. The city features various neighbourhoods, including the historic district and the waterfront area, which offer great experiences. Many of these properties provide spacious living rooms, fully equipped kitchens for family meals, and outdoor spaces for children to play.Additionally, visitors can enjoy nearby attractions such as the Beardsley Zoo, which is great for a family outing, and the scenic Seaside Park, superb for picnics and enjoying nature. With amenities like Wi-Fi, air conditioning, and sometimes even game rooms, families can expect a comfortable stay while exploring all that Bridgeport has to offer.
Are there pet-friendly house rentals in Bridgeport?
In Bridgeport, there are several pet-friendly house rentals available, offering a variety of amenities for travellers. Many of these properties feature spacious layouts, fully equipped kitchens, and outdoor spaces such as patios or gardens, superb for enjoying the fresh air with your furry companions.The neighbourhoods around the waterfront, particularly near Seaside Park, provide easy access to green spaces where pets can enjoy walks and playtime. Seaside Park itself is a beautiful area with walking trails, sandy beaches, and plenty of open space, making it an excellent spot for pet owners. Additionally, the nearby Beardsley Zoo offers a unique outing, although pets are typically not allowed inside, the surrounding areas provide ample opportunities for leisurely strolls.
Are there any remote work holiday rentals in Bridgeport?
In Bridgeport, Connecticut, there are numerous remote work holiday rentals available, with around 141 options to choose from. These properties are well-suited for those looking to combine work and leisure, featuring amenities such as high-speed internet and Wi-Fi, ensuring a reliable connection for remote work. Many rentals also include dedicated workspaces with desks and comfortable chairs, allowing for a productive work environment.The city itself is rich in cultural attractions, including the Bridgeport Downtown area, where visitors can enjoy local dining, shops, and the scenic waterfront. Additionally, the nearby Beardsley Zoo provides a fun outing for those taking breaks from work, making this city a lively and convenient choice for remote workers. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Bridgeport?
In Bridgeport, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also offer onsite parking, which is convenient for those travelling by car. Additional amenities often featured are coffee and tea makers for a comforting start to the day, desks for those needing to work or study, and the option for pets to be permitted, making it easier for travellers to bring their furry companions along.
When is the best time to visit Bridgeport for a holiday rental?
The best time to visit Bridgeport for a holiday rental is during the peak season from May to July, with July being particularly popular. This vibrant period welcomes travellers, as the warm summer weather creates ideal conditions for enjoying the beautiful coastal attractions and outdoor activities that Bridgeport has to offer.During these months, you can take advantage of comfortable temperatures, typically ranging from 20 to 30 degrees Celsius, superb for beach days, picnics in the parks, and exploring local attractions like the Beardsley Zoo and the Maritime Aquarium. The lively option is enhanced by various summer events and festivals, making it a wonderful time for creating lasting memories with family and friends.If you're looking for a more budget-friendly option, consider planning your visit in December. While the weather can be cooler, with temperatures hovering around 0 to 5 degrees Celsius, the festive holiday spirit in Bridgeport brings a unique charm to the city. You can enjoy the twinkling lights and seasonal celebrations, all while avoiding the larger crowds of the summer months.Ultimately, your ideal time to visit Bridgeport will depend on whether you prefer the bustling energy of the peak season or the quieter, more intimate experiences of the winter months.
What are the top attractions in Bridgeport?
In Bridgeport, visitors can explore a variety of attractions that cater to diverse interests. The Beardsley Zoo, located in the Beardsley Park neighbourhood, is a highlight, featuring a range of animals and a beautiful setting for families. Nearby, the park itself offers walking trails and picnic areas, making it a great spot for outdoor activities.For those interested in the arts, the Downtown area is home to the Housatonic Museum of Art, which boasts an impressive collection of American and European art. The historic Barnum Museum, dedicated to the life of P.T. Barnum, is also a must-see, showcasing artefacts and exhibits related to the famous showman.The scenic waterfront at Seaside Park provides a lovely backdrop for leisurely strolls, picnics, and beach activities during the warmer months. Visitors can also enjoy the vibrant setting of the Bridgeport Bluefish baseball games at the Ballpark at Harbor Yard, which adds to the local sports culture.
Are all fees included in the Bridgeport holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Bridgeport holiday homes with parking?
Stayz offers a wide selection of holiday homes in Bridgeport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Bridgeport holiday homes?
You can find great discounts on holiday homes in Bridgeport on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Bridgeport holiday home booking on Stayz?
To find Bridgeport holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Bridgeport?
A long-stay holiday home in Bridgeport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Bridgeport holiday home?
Book your Bridgeport holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Bridgeport?
Prices for holiday homes in Bridgeport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Bridgeport to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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