Waterfront vacation rentals in Bridgeport

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Top-rated waterfront rentals in Bridgeport

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Apartment in Milford
4.97 out of 5 average rating, 606 reviews

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!

Top guest favorite
A serene view of the Long Island Sound showcases several sailboats gently drifting on the blue water. The scene is framed by a simple fence and grassy area, with a clear blue sky above, creating a peaceful coastal atmosphere.
Home in East Shore
4.98 out of 5 average rating, 192 reviews

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

PETS ALLOWED! Spectacular unobstructed Long Island Sound views year-round, out your front door along Pardee Seawall! This exceptional shore line property offers all new furniture & amenities. Minutes to wedding venues-perfect for getting dressed on your wedding day & taking photos literally right outside your door (props available). Near: Tweed NH Airport, beach, Yale University & Hosp, restaurants & museums. All new furniture, linens/towels, grill, fire pit, centralAC, WIFI. Onsite parking.

Top guest favorite
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.
Home in Milford
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.

Top guest favorite
Apartment in Milford
4.98 out of 5 average rating, 129 reviews

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.

Top guest favorite
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
4.94 out of 5 average rating, 164 reviews

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.

Guest favorite
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.
Home in Milford
4.96 out of 5 average rating, 246 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!

Top guest favorite
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
4.97 out of 5 average rating, 181 reviews

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

Top guest favorite
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.
Home in Milford
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!

Top guest favorite
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.
Guesthouse in Waccabuc
4.98 out of 5 average rating, 117 reviews

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)

Top guest favorite
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
4.97 out of 5 average rating, 414 reviews

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..

Guest favorite
An aerial view showcases the Candlewood Lakeview Estate, framed by lush greenery highlighting the surrounding landscape. The expansive lake reflects the sky, while the custom home features a brick exterior. Key outdoor amenities are subtly integrated into the picturesque environment.
Home in Danbury
4.95 out of 5 average rating, 111 reviews

Lakeview Estate - Chef's Kitchen - NYC Getaway

Stunning lake views from every angle! Gorgeous 3,200 square foot custom home with an open floor plan. Highlights include: * Chef's kitchen with Viking Range, Sub Zero Refrigerator, granite countertops & custom cabinets * Expansive 20x30 stone patio overlooking the lake with a fire-pit, speakers & outdoor lighting * 3 spacious bedrooms and 3 full bathrooms with double vanities, showers & separate bathtubs. * 5 SmartTVs including a 65" TV in the main living area

Guest favorite
A two-story oceanfront home features a light gray exterior with large windows and a turquoise front door. A spacious ground level is accessible via white railings, leading to an outdoor sitting area. The serene beach and water views are visible in the background.
Home in Milford
4.96 out of 5 average rating, 117 reviews

Oceanfront Retreat with Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

Popular amenities for Bridgeport waterfront rentals

Quick stats about waterfront rentals in Bridgeport

  • Total vacation rentals

    Explore 10 vacation rentals in Bridgeport

  • Nightly prices starting at

    Bridgeport vacation rentals start at $50 per night before taxes and fees

  • Verified guest reviews

    Over 370 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Bridgeport vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Bridgeport rentals

  • 4.7 Average rating

    Bridgeport stays receive an average rating of 4.7 out of 5 from guests

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