Waterfront holiday rentals in Bridgeport

4.96 out of 5 average rating, 111 reviews

The exterior of the modern chalet is surrounded by lush greenery, showcasing a spacious sun room with large windows. A hammock is visible between trees, inviting relaxation. The property features a gently sloping yard leading down to the tranquil lakefront.

Chalet in Carmel Hamlet

Secluded Lakefront Chalet-Firepit+Yard Dogfriendly

Just over an hour from NYC, this secluded, dog-friendly lakefront chalet offers 200’ of private shoreline, fenced yard and sunroom with stunning lake views. Thoughtfully decorated with treasures from my travels, it blends quiet luxury and modern comfort. Cozy up by the fireplace, enjoy a vinyl or a movie, take in Autumn colors, spot local wildlife, hike nearby trails, unwind by the fire pit and rest in the king size bed. Romantic, peaceful, beautifully secluded – your perfect fall escape awaits.

4.97 out of 5 average rating, 609 reviews

An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.

Flat in Milford

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.

4.98 out of 5 average rating, 134 reviews

3 Bedroom Beach House with Hot Tub!

Enjoy breathtaking sunset views in our spacious beach house while dining or relaxing in the hot tub. Snuggle up in front of the fireplace while watching a movie on the frame TV. Wake up in the master suite to spectacular marsh views while listening to birds from the Audubon Society. Steps to a white sand beach, heated bathroom floors, luxury bathrobes, linens, and organic mattresses. 6-bikes for exploring. A true resort-like experience with a chef's kitchen making a home away from home.

4.98 out of 5 average rating, 132 reviews

Flat in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

4.91 out of 5 average rating, 214 reviews

A spacious living area features a large sectional sofa adorned with decorative pillows, complementing a dining area with a round table and four chairs. Bright overhead lights illuminate the space, which includes a modern kitchen visible in the background.

Guest house in Milford

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

4.94 out of 5 average rating, 167 reviews

A serene waterfront view is presented, showcasing calm waters reflecting a soft pink sky. Lush green grasses frame the foreground, while a tree line marks the horizon, creating a tranquil landscape. A few ducks can be seen gently floating on the water.

Loft in Milford

Lovely water front lower-level loft, free parking

This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

4.96 out of 5 average rating, 248 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

4.97 out of 5 average rating, 187 reviews

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

An aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.

5 out of 5 average rating, 116 reviews

Steps2Beach, Fish Pond, Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

4.98 out of 5 average rating, 119 reviews

The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.

Guest house in Waccabuc

French Guest House in Waccabuc

A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

4.96 out of 5 average rating, 417 reviews

A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.

Cabin in Sherman

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

4.93 out of 5 average rating, 134 reviews

The exterior of a beach cottage is shown, featuring light-colored siding and blue shutters. A white railing surrounds a small porch, leading to a front door. Lush greenery and a few decorative elements enhance the inviting appearance of the home.

Cottage in Milford

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Peaceful Classic1920s Milford beach cottage steps from Silver Sands Beach & boardwalk. Blending coastal charm with modern comfort, it’s perfect for vacations, remote work, or longer stays. Walk to downtown shops, restaurants, and train. Ideal for Yale visitors, travel nurses, or weekend getaways. Enjoy a private, pet friendly retreat surrounded by nature yet close to New Haven, NYC, and Connecticut’s best shoreline attractions

Popular amenities for waterfront rentals in Bridgeport

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.97 out of 5 average rating, 34 reviews

A bright studio space is occupied by a spacious bed adorned with various green cushions. A kitchenette with modern appliances, including a microwave, is visible in the corner. Natural light filters through the windows, highlighting the decorative elements on the walls and floor.

Flat in Branford

Stony Crk Studio ideal for trvl nurses…

4.95 out of 5 average rating, 22 reviews

A peaceful beach scene captured at night reveals a sandy shoreline reflecting moonlight. Houses line the beach, their warm lights creating a welcoming glow. Calm waters extend to the horizon, while scattered clouds drift in a starry sky, enhancing the serene coastal atmosphere.

Flat in Milford

Seasonal Experiences that Keep it Local! Book NOW!

4.99 out of 5 average rating, 155 reviews

The bedroom features a queen bed with a colorful marine-themed bedding set. Light blue walls complement the natural wood flooring. Two windows allow ample natural light, with blinds for privacy. Decorative elements include beach-themed art, a nightstand, and a dresser.

Flat in Northport

Amazing one bdrm flat at the beach!

5 out of 5 average rating, 78 reviews

The exterior of a historic brick building displays vibrant red accents and festive decorations. American flags are hung on the facade, with a decorative wreath on the door. Showcasing a welcoming entrance, the space is complemented by a brick pathway leading to the door.

Flat in Wall Street

Phoenix Engine #1

4.96 out of 5 average rating, 98 reviews

A spacious living area features a large sectional sofa adorned with red cushions, complemented by a coffee table and side tables. Bright light floods the room through the sliding glass doors, opening to the outdoor deck. A staircase leads to a lofted area, enhancing the open feel.

Flat in Guilford

Cozy Private Lake Q Retreat

4.85 out of 5 average rating, 212 reviews

A wooden dock extends into the water, lined with boats gently bobbing on the surface. Lush green hills rise in the background, while a clear blue sky with scattered clouds frames the scene. People are gathered along the dock, enjoying the views.

Flat in Northport

Harbor Studio - Across from historic Northport doc

Superhost

A comfortable living area features a black sofa and a light-colored couch with decorative pillows. A wooden coffee table sits at the center, surrounded by a small dining table and chairs. Soft lighting is provided by a stylish fixture, and natural light enters through the windows.

Flat in South Norwalk

4.88 out of 5 average rating, 100 reviews

Water View SONO 2 Bedroom Walk to Metro & Dining

5 out of 5 average rating, 83 reviews

A well-maintained exterior of a two-story home features a welcoming porch with white railings and an American flag. Lush green landscaping surrounds the front, with vibrant flower beds and several large windows allowing natural light inside.

Flat in Fairfield

Bright, private 1,000 sq. ft. 1-Bedroom Apartment

Waterfront house rentals

The exterior of a newly constructed home features a combination of blue and white siding. Large windows are present on multiple levels, allowing for ample natural light. A staircase leads to the entrance, while parking is available beneath the house.

4.86 out of 5 average rating, 63 reviews

Newly Built Beach House Getaway

4.93 out of 5 average rating, 121 reviews

A serene view of Squantz Pond is framed by lush greenery, with vibrant trees and neatly trimmed grass in the foreground. The tranquil water reflects the sky, creating a peaceful atmosphere, while a private dock is visible along the water's edge.

Home in New Fairfield

Beautiful Lakefront Retreat with Private Dock

Superhost

Home in New Milford

4.91 out of 5 average rating, 117 reviews

The Getaway: Beautiful Waterfront - New Milford CT

4.8 out of 5 average rating, 359 reviews

A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.

Home in Port Jefferson

The Hilltop Harborview

4.97 out of 5 average rating, 100 reviews

The kitchen features modern cabinetry with a contrasting dark granite island. Three cushioned stools are positioned at the island. Natural light enters through a window above the sink, illuminating new stainless steel appliances and a sleek backsplash. A door leads to the outdoor area.

Home in Black Rock

Cape on the Water

4.95 out of 5 average rating, 167 reviews

An inviting waterfront deck is displayed, featuring two lounge chairs with striped fabric and a small table. A fire pit sits nearby, surrounded by a clear view of the bay, where sailboats are gently anchored. Lush greenery lines the horizon, enhancing the serene atmosphere.

Home in Centerport

The Harbor House: Beachfront Home 1 hour from NYC

The cottage exterior features a welcoming red door and white adirondack chairs on the porch, inviting relaxation. A cozy fire pit is surrounded by stone in the yard, while vibrant flowers cascade nearby. An aerial view highlights the coastline and neighborhood layout, showcasing proximity to water.

4.97 out of 5 average rating, 90 reviews

Seaside Cottage: water views, walk to beaches!

4.95 out of 5 average rating, 124 reviews

A vibrant sunset reflects on calm waters, with shades of orange and purple illuminating the sky. Silhouettes of small boats are visible along the sandy shoreline, while gentle waves create a serene atmosphere. The scene offers a tranquil view of Long Island Sound at dusk.

Home in East Shore

Beach Haven - waterfront, near Yale, sunsets

Other waterfront holiday rentals

4.95 out of 5 average rating, 44 reviews

Cottage in Lordship

Waterfront Beach Cottage in Connecticut

5 out of 5 average rating, 11 reviews

Cabin in Madison

Riverfront Antique Cabin in the Heart of Madison

4.94 out of 5 average rating, 82 reviews

A rustic exterior of a large studio is framed by trees showcasing fall colors. The structure features a unique design with a gabled roof and wooden paneling. A gravel driveway and a stone patio are visible, providing access to the entrance amid a serene natural setting.

Guest house in Southbury

The Nest. Large studio in the Woods.

Superhost

An inviting living area features a stone fireplace accompanied by a large flat-screen TV. Colorful artwork and decorative accents include modern furniture and plush seating. Large windows allow natural light to fill the space, while a dining area is visible in the background.

Villa in Bridgeport

4.81 out of 5 average rating, 16 reviews

Indulge in Prime Luxury 3BR 3-7 Guest

Guest house in East Norwalk

A modern kitchen features a central island with a sleek cooking range and ventilation hood. Bright windows provide views of Norwalk Harbor and the surrounding landscape. Light cabinetry complements the stainless steel appliances, creating a clean and airy space for meal preparation.

5 out of 5 average rating, 31 reviews

Waterfront Getaway - Norwalk, CT

Guest house in Bedford Hills

The cottage is tucked amidst vibrant autumn foliage, framed by trees. A large front deck, furnished with two chairs, provides a serene entry, while the three expansive windows invite natural light. The wooden exterior blends harmoniously with the surrounding woodland.

5 out of 5 average rating, 70 reviews

The Perch, a luxe cottage in the woods 1h from NYC

4.95 out of 5 average rating, 66 reviews

A quaint beach cottage is elevated on stilts above a paved area. A wooden deck with a railing wraps around the entrance, leading to an inviting front door. Surrounding grass and a glimpse of the water can be seen in the background.

Cottage in Lordship

Connecticut Beach Cottage on The Long Island Sound

A beachfront view of a multi-story house showcases a white exterior with balconies overlooking the sand. A patio area with seating and a grill is visible in the foreground, while ample sandy beach extends before the property, under a partly cloudy sky.