Waterfront holiday rentals in Fairfield

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.

4.97 out of 5 average rating, 605 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!

4.98 out of 5 average rating, 128 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.

4.94 out of 5 average rating, 162 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.

4.93 out of 5 average rating, 128 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

Classic 1920s beach cottage perfect for your summer at the shore! It is tucked away on a quiet street, across from Silver Sands Beach Milford. This cozy cottage offers 2 bedrooms with bonus loft sleeping area. In one of CT's most desired shoreline locations, steps to the private beach & Silver Sands State Park boardwalk, walnut beach, ice cream and cafe. Close to downtown green which offers bars and restaurants, train to NYC and New Haven, Yacht Clubs and Yale. Beach Vacation. Pet Friendly!

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, 245 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!

4.94 out of 5 average rating, 123 reviews

A tranquil outdoor scene features a lush green lawn surrounding a calm pond. The reflection of trees and the nearby home can be seen in the water. A picnic table sits on the grass, inviting relaxation amidst the natural surroundings.

Home in Southington

Connecticut Chalet: Experience Fall in New England

Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

4.98 out of 5 average rating, 103 reviews

A spacious interior is showcased, featuring a combination of natural wood walls and high, vaulted ceilings with exposed beams. A comfortable seating area is observed, complemented by a rustic dining space with wooden furniture and warm lighting, creating an inviting atmosphere.

Guest house in Redding

Little Blue Heron-Idyllic log cabin w/hot tub!

Amazing log cabin cottage, nestled across a picturesque bridge and waterfall on the serene Blue Heron Hollow estate! Featuring, outdoor natural stone fire pit, propane BBQ and brand new Life Smart hot tub! With wifi, parking and firewood, provided free of charge! Biking, hiking, hunting, horseback riding, wine tasting, pickleball and seasonal apple & pumpkin picking, all nearby! I’m a long time Super Host who took a break and now so excited to reopen Little Blue Heron to you all!

4.97 out of 5 average rating, 180 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!

4.99 out of 5 average rating, 114 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)

4.97 out of 5 average rating, 413 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..

Place to stay in Southport

A spacious bedroom features a large bed with crisp white linens, surrounded by vibrant artwork and colorful cabinetry. Warm wood paneling lines the ceiling, and two bedside lamps provide soft illumination, contributing to a bright and inviting environment.

4.95 out of 5 average rating, 329 reviews

Sunny Westport 2 BR Retreat above Historic Mill

Historic Cider Mill Retreat – A Unique Stay for Leisure & Business Travelers Experience the charm of history blended seamlessly with modern comfort in this eclectic, sun-filled apartment perched atop a beautifully restored 1850s cider mill. Thoughtfully designed and furnished by our team of artisans, this unique getaway offers panoramic views, breathtaking surroundings, and a rich historical ambiance that makes for a truly unforgettable stay.

Popular amenities for waterfront rentals in Fairfield

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

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.

4.95 out of 5 average rating, 20 reviews

Seasonal Experiences that Keep it Local! Book NOW!

4.99 out of 5 average rating, 154 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, 77 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

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

4.94 out of 5 average rating, 52 reviews

A spacious room features warm hardwood floors and large windows allowing natural light. A king size bed is adorned with light bedding and soft pillows. A comfortable sofa can be seen in the background, alongside a wooden coffee table and plants, fostering a relaxed atmosphere.

Flat in Stamford

Spacious. Water Views & Access. Steps to Beach.

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.

4.96 out of 5 average rating, 76 reviews

Steps to the Beach. Lovely 2-Bedroom apt

4.86 out of 5 average rating, 181 reviews

Two paddleboats are moored next to a wooden dock, resting on calm waters. The boats feature a blue color with a simple design, and the dock extends towards the lake, reflecting the peaceful setting.

Flat in Middletown

Lakeside apartment 2.5 miles from Wesleyan campus!

Waterfront house rentals

4.91 out of 5 average rating, 113 reviews

Home in New Milford

The Getaway: Beautiful Waterfront - New Milford CT

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

5 out of 5 average rating, 11 reviews

The kitchen features modern appliances set against white cabinetry, complemented by black bar stools. An outdoor gathering area showcases a circular fire pit surrounded by black Adirondack chairs, with waterfront views in the background. A cozy bedroom displays a large bed with decorative pillows and natural light filtering through the window.

Home in Stratford

Charming Riverview Home*Firepit* Near Train & I-95

4.97 out of 5 average rating, 98 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

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.

4.96 out of 5 average rating, 116 reviews

Oceanfront Retreat with Hot Tub

5 out of 5 average rating, 26 reviews

A spacious living area is furnished with a cozy striped sectional sofa, complemented by a rustic wooden coffee table. Bright natural light filters through the windows, enhancing the neutral decor. Bar stools are arranged at a counter in the background, providing additional seating.

Home in Weston

River Cottage in Weston, CT

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

4.99 out of 5 average rating, 330 reviews

A cozy living area is presented, featuring a spacious gray sofa and two vibrant orange chairs. A coffee table rests atop a colorful area rug, with natural light filtering in through large windows. Green foliage is visible outside, enhancing the welcoming ambiance.

Home in Fair Haven

Q River House - 2 bdrm, minutes from Yale/Downtown

Other waterfront holiday 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.

4.85 out of 5 average rating, 62 reviews

Newly Built Beach House Getaway

4.95 out of 5 average rating, 43 reviews

Cottage in Lordship

Waterfront Beach Cottage in Connecticut

4.94 out of 5 average rating, 17 reviews

Home in Fairfield Beach

Beachfront House In Fairfield *private beach*

5 out of 5 average rating, 12 reviews

An open living area features a spacious layout with a light-colored sofa and a wooden dining table. Large windows offer views of the water, while recessed lighting brightens the room. A contemporary fireplace is positioned beneath a wall-mounted television, creating a cozy focal point.

Cabin in Bayville

Beautiful Waterfront Cottage

Superhost

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.

Cottage in Milford

4.87 out of 5 average rating, 89 reviews

Cheerful 3 Bedroom Cottage with Fire Place

4.96 out of 5 average rating, 82 reviews

An outdoor seating area is featured with two ornate egg chairs and a spacious sofa. The furniture is complemented by colorful cushions, and a geometric patterned rug is placed underneath. A stone fireplace is visible in the background, surrounded by trees.

Home in New Fairfield

Hilltop Retreat- Lakefront with Dock

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, 30 reviews

Waterfront Getaway - Norwalk, CT

The exterior of a two-story beach house is displayed, featuring a light-colored facade with a welcoming front porch and a gravel driveway. Inside, bright, open living spaces include a modern kitchen with sleek black appliances, a comfortable living area with a sofa, and a serene bedroom filled with natural light.