Beachfront holiday rentals in Fairfield

Two colorful sailboats glide across the water, their vibrant sails displaying shades of orange, yellow, and blue. In the background, a green tree line is visible along the shore, suggesting a natural setting.

4.94 out of 5 average rating, 143 reviews

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

5 out of 5 average rating, 33 reviews

A charming home is set in a lush green landscape, showcasing a well-maintained front yard with a pathway leading to the entrance. The facade features large windows framed by dark trim and is complemented by colorful flower arrangements on the porch. Mature trees provide a natural canopy.

Home in New Haven

Historic Home on the Harbor!

Private Home Facing New Haven Harbor! This Eastlake Victorian is uniquely positioned in the tranquil Oyster Point Historic District! Perks of the Property: - Water views of Long Island Sound / New Haven Harbor! - Back deck, patio, and mature gardens. - Clawfoot Tub in main bathroom! - A few doors down from Shell and Bones Restaurant, Little Lotus Sushi, and the Pequonnock Yacht Club. - Easy commute to Union Station, Yale New Haven Hospital, Yale University, and I-95 / I-91 Highways.

4.89 out of 5 average rating, 243 reviews

The exterior of a two-story beach cottage is visible, featuring a soft gray facade and a balcony on the upper level. Large windows illuminate the lower floor, surrounded by a well-kept lawn and garden. A decorative trellis adds character to the welcoming entryway.

Home in East Haven

Beach Cottage by the Sea

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

5 out of 5 average rating, 4 reviews

Home in North Salem

Pet Frndly Lake House w/Fireplace & Fire Pit W/D

Relax with the whole family at this peaceful place to stay. You’ll enjoy a yard, parking for 2 cars, fire pit, BBQ grill and a peaceful neighborhood where you can enjoy day walks. Your pets are welcome during your stay- we will ask about the breed and size- pets are not allowed on the beds or couch. You also have access to the lake just steps from this home. Train station is just 10 min away. Enjoy the farms, restaurants and scenery of North Salem, a place where your whole family can enjoy!

4.92 out of 5 average rating, 106 reviews

A lakeside patio is depicted, featuring several metal chairs arranged around a firepit. Two swinging chairs hang from a pergola, while a dock with a boat and kayak is visible on the water. A vibrant American flag flutters in the background.

Guest suite in Newtown

waterfront on Lake Zoar[ SUITE]

Enjoy your private patio overlooking the lake, Or just walk 12 steps to water Edge and visit the cozy lower level and enjoy the swings . Use our kayaks, and don’t forget to bring your fishing pole, go swimming ,or just sit in the sun with a book and listen to the waterfall and you are welcome to sit by the firepit Optional boat dock space, parking Hosts live upstairs Two miles to quaint Sandy Hook center with grocery and restaurants All quests must be register Ninety minutes to Boston/nyc

4.96 out of 5 average rating, 55 reviews

A tranquil view of a private beach stretches along the coastline, where gentle waves lap against the smooth sand. Soft clouds dot the blue sky, while beach houses stand in the background, providing a serene coastal ambiance.

Home in Morgan Point

Direct Beachfront Modern Cottage on Private Beach

A Modern Beachfront 3-Bedroom House RIGHT ON WATER! AT A GLANCE: ➤ 10 seconds to water ➤ Private beach to enjoy swimming, kayaking, and strolls along the Long Island Sound ➤ Fully updated well stocked kitchen ➤ Grill for outdoor BBQ's ➤ Large deck to catch some rays ➤ Outdoor shower to rinse off ➤ New AC units & ceiling fans throughout ➤ Large TV w/ AppleTV connectivity & WIFI ➤ Only 90 min to NYC, close to Yale in New Haven ➤ Hosted by an experienced Superhost ➤ Sorry, No pets allowed.

4.95 out of 5 average rating, 126 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

Everything you need for an amazing vacation, year-round, in our comfortable home right on the beach! Walk out the back door and dip your toes in the sand and in Long Island Sound. Enjoy spectacular views from the back patio, sun room, and most rooms in the house. Watch the sunset while soaking in the hot tub. Sit by the gas fireplace with a book. Stroll along the lovely nearby sea wall. 10-minute drive to Yale and all downtown New Haven has to offer. 5-minute drive to Lighthouse Point Park.

4.98 out of 5 average rating, 208 reviews

An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.

Home in Branford

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Two wicker chairs with patterned cushions are positioned beside a large window, offering a panoramic view of the sandy beach and ocean. The serene landscape includes gentle waves and distant beachgoers, framed by a bright sky.

4.99 out of 5 average rating, 145 reviews

Serene Waterfront Retreat - 400 ft Private Beach!

Welcome to a slice of waterfront heaven! Located on Milford's Cedar Beach, this newly renovated 3 bedroom / 1.5 bath home features over 400 feet of private beach. Enjoy breakfast prepared in the Chef's kitchen while watching one of the most radiant sunrises you will ever see. Stunning views from every room in the house. Wade into Long Island Sound with your own private beach. Located 3 doors down from the CT Audubon Society, known for its views & wildlife. We can't wait to host you!

A view of Long Island Sound at sunset is captured from the balcony. Gentle waves reflect the colors of the sky, ranging from soft pink to deep orange, while Charles Island is visible in the distance, framed by the serene horizon.

5 out of 5 average rating, 108 reviews

Milford Beach House - Newer Construction!

Relax on the beach! Recently built 3 bdrm home (2300 square foot) on the beach facing Long Island Sound w/ view of Charles Island! Silver Sands State Park 30 yards away! Big deck! Restaurant within walking distance & plenty more a short drive away. Park up to 4 vehicles below the house. This is a stylish beach house with loads of windows! Views, location and ambiance! Great for couples, adventurers, families & small groups. Dogs are welcome with pet fee.

Cottage in Fairfield Beach

4.98 out of 5 average rating, 126 reviews

Charming Fairfield Beach Cottage

Escape to our newly renovated waterfront cottage in Fairfield, just steps from a private beach on the Long Island Sound. This charming retreat is perfect for families and couples, offering a modern kitchen, private deck, and high-speed WiFi. Unique perk: Enjoy complimentary 24/7 access to a beautiful co-working space just 3 miles away. A perfect blend of relaxation and productivity awaits!

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

Brand new home on the beach near Silver Sand State park full of upgrades and incredible views from everywhere. Additional features including built in speakers throughout the house, chef style kitchen, fireplace, balconies on all levels, roof top deck. Parking underneath house. 1.4 miles from downtown shops, restaurants and bars as well as train into NYC.

Popular amenities for beachfront rentals in Fairfield

Kitchen

Wifi

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Flat in South End

4.52 out of 5 average rating, 87 reviews

Historic Brownstone Close to Beach & Amphitheater

A small outdoor seating area is visible, featuring two chairs positioned around a circular table. A bottle of beer and two wine glasses sit on the table. Soft outdoor lighting hangs from nearby trees, casting a warm glow over the serene riverbank and surrounding greenery.

Cabin in Southbury

4.75 out of 5 average rating, 225 reviews

River Stone Hollow

5 out of 5 average rating, 3 reviews

New England Beach House

Bungalow in Fairfield Beach

New place to stay

Steps to Beach-Water View-Pet Friendly-Fenced Yard

A wooden walkway extends past a bicycle towards a scenic view of the ocean. The railing lines the pathway, which leads to the water's edge, with a clear blue sky above and distant greenery visible along the coast.

4.8 out of 5 average rating, 5 reviews

3 Bedroom Private Beachfront Hideaway KO

An aerial view of a small beach bungalow positioned near the coast is shown. The image highlights the proximity to the water and surrounding neighborhoods, with residences and a sandy shoreline visible in the background. The tranquil blue tones of the ocean contrast with the greenery of the nearby landscape.

Home in West Haven

4.77 out of 5 average rating, 99 reviews

Beachy Bay Breeze Bungalow 2BR with parking and close to many amenities.

An exterior view of the designer beach house is captured, showcasing its contemporary blue siding and multiple windows. A rooftop deck is visible, providing potential outdoor space. A grassy area is bordered by a white privacy fence, while neighboring structures can be seen in the background.

4.88 out of 5 average rating, 41 reviews

Bohemian Beach Oasis- Private Beach

The exterior of the three-story house is clad in grey shingles, accented by a vibrant turquoise front door. Multiple windows allow natural light into the interior, framing a modern yet classic architectural style.

4.93 out of 5 average rating, 28 reviews

Long-term Stay, Light filled Beach Household

Private beachfront home rentals

A two-story cottage features horizontal siding and a distinctive light blue front door. A large window is positioned above the entrance, allowing natural light to enter. The garage is on the ground level, with a small staircase leading to the entryway.

4.93 out of 5 average rating, 55 reviews

Salty Kisses Beach Cottage Milford CT

4.97 out of 5 average rating, 37 reviews

A charming entrance reveals a light-colored house with a teal door, framed by green landscaping. A pathway leads to the steps, flanked by decorative flowerpots. A large tree provides shade, while an American flag is displayed on the right side, complementing the inviting atmosphere.

Bungalow in Milford

A BREATHTAKING AND RELAXING PLACE TO CALL HOME

A charming beach cottage is visible from the water, featuring a white exterior and a welcoming front porch with railings. A set of stairs leads down to the sandy beach area, where a green chair and small table are situated, ideal for relaxation by the shore.

4.88 out of 5 average rating, 152 reviews

Waterfront Beach Cottage

The elevated property features a sturdy deck with wooden railings, accessible by a wide staircase. Surrounding grassy areas and a large tree provide shade, while the building’s exterior is composed of light-colored siding, situated amid other residential structures.

4.89 out of 5 average rating, 38 reviews

Welcome to your perfect coastal getaway!

4.67 out of 5 average rating, 3 reviews

Beachfront Paradise Amazing water views

4.88 out of 5 average rating, 24 reviews

A tranquil view of the water is framed by tall trees, reflecting sunlight over the surface. Several docks are visible in the distance, accommodating boats. The scene captures the serene ambiance of the waterfront, surrounded by greenery.

Cottage in Danbury

Lakefront cottage on Candlewood Lake

A light-filled living room is presented, featuring a neutral-colored sofa paired with a round, woven coffee table. Chairs are positioned nearby, and greenery adds a touch of nature. The space includes shelves adorned with decorative items and a wall-mounted art piece, enhancing the cozy ambiance.

4.83 out of 5 average rating, 60 reviews

New England Beach cottage

4.96 out of 5 average rating, 76 reviews

A two-story beach apartment is shown with a light blue exterior and white railings. A staircase leads up to a front deck, surrounded by colorful flower beds. Large windows on the upper level provide ample natural light, while an inviting entrance is seen below.

Flat in Milford

Steps to the Beach. Lovely 2-Bedroom apt

Luxury beachfront home rentals

4.97 out of 5 average rating, 35 reviews

A spacious living area is furnished with comfortable seating options in neutral tones. Large windows provide unobstructed views of the waterfront, letting in ample natural light. Ceiling fans enhance the air circulation, while hardwood floors add warmth to the space.

Home in West Haven

Beautiful, Spacious, Waterfront Home on the Bay

A two-story building with gray siding and white trim is positioned on a quiet street. The structure features a wraparound porch and green door. The distance to the ocean is visible, with water beyond the nearby structures and a clear sky overhead.

4.9 out of 5 average rating, 77 reviews

Beach house - Sapphire Sandbar

4.92 out of 5 average rating, 64 reviews

A spacious outdoor deck overlooks the tranquil waters of Long Island Sound, featuring comfortable lounge seating and a fire pit. The serene beach is visible in the background, framed by lush greenery, inviting relaxation and outdoor gatherings under the open sky.

Home in Morgan Point

Oceanfront Getaway - Quiet, Firepit + Pvt Beach

4.96 out of 5 average rating, 26 reviews

A large beach house is visible, featuring multiple gables and a spacious deck with balcony. The facade is painted in light grey, complemented by white trim. In the foreground, sandy beach leads toward the house, framed by green grass and shrubs on either side.

Home in West Haven

Beach House steps from sand & Amazing Views

A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.

4.87 out of 5 average rating, 90 reviews

Cheerful 3 Bedroom Cottage with Fire Place

Home in Fairfield

New place to stay

Pine Creek Beach House

A shaded porch featuring a gray wooden floor extends towards the water, with hanging planters displaying vibrant flowers. Ocean views are visible in the distance, and a small blue boat is anchored along the shoreline. Soft light creates gentle shadows across the space.

4.96 out of 5 average rating, 49 reviews

Beachfront paradise- come, stay, relax!