House holiday rentals in Milford

An expansive wooden deck features a circular picnic table with attached benches, overlooking coastal views. The area is bordered by a railing, and additional seating options are visible. A clear sky and soft clouds provide a serene backdrop.

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, 140 reviews

Fully renovated/Walk to water & shops/fenced yard!

*Feb and Mar available for longer stays!Inquire!* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speed

The third-floor balcony features a spacious outdoor sectional and a high-top table, inviting relaxation with panoramic views. Glass railing enhances the feeling of openness, while a cozy seating area inside allows for indoor comfort. Natural light fills the area, complemented by modern design elements.

4.97 out of 5 average rating, 71 reviews

Luxury Beach Oasis with Amazing Ocean Views

Welcome to our stunning 4 bedroom beach house, just a stone's throw away from the beach. This meticulously designed home offers a seamless blend of modern comfort and beachside charm. An open-concept layout, perfect for unwinding after a day spent on the beach. Wake up to the sound of seagulls and the scent of the ocean, while sipping your morning coffee, or unwind with a glass of wine taking in amazing views on the balcony. Book your seaside escape and let the waves of relaxation wash over you.

A serene beach scene captures the sun setting over calm waters. Soft golden light reflects off the surface, with silhouettes of wooden posts extending into the tide. The shoreline is framed by sand, creating a peaceful atmosphere for nature appreciation.

4.93 out of 5 average rating, 42 reviews

* Walk to Beach, Pet-Friendly, Near Tyde

-A brief walk to Wildemere (3 minutes) or Walnut Beach (10 minutes) to enjoy the sun and water. -7 minute walk to the new Tyde at Walnut Beach!!! This peaceful beach community is welcoming and ready for you to explore. Take a stroll to the coffee shop, restaurants, beach boardwalk, and the BEST ice cream shop-Walnut Beach Creamery. Maybe cook or order in to relax on the beautiful patio by the fire pit while the kids have s’mores! -quick drive to famous pizza and hiking and farms -train to NYC

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, 118 reviews

Walnut Beach Escape Fenced Oasis Yard

🌊 Steps from Walnut Beach & Silver Sands State Park, this guest-favorite coastal escape blends beach access, privacy & relaxed luxury. Enjoy a tropical-inspired backyard oasis with a cascading fish pond, multiple lounge areas & a seasonal palm tree—perfect after a day by the shore. Inside, unwind in a beautifully designed home with a gourmet kitchen & modern comforts. Just 90 minutes from NYC & 15 from New Haven, it’s an ideal retreat for beach days, nature lovers & laid-back coastal living.

4.98 out of 5 average rating, 210 reviews

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 New Haven

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.

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.

4.97 out of 5 average rating, 150 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.

An aerial view captures the surrounding residential neighborhood with close proximity to Long Island Sound. The property is highlighted in a circular outline, showcasing its location relative to nearby homes and the shoreline.

4.97 out of 5 average rating, 110 reviews

2 Bedroom with sweeping views of Long Island Sound

Entire 1st floor apartment with private entrance. A spacious layout with spectacular views of Long Island Sound from your private deck. Convenient location; minutes to downtown Milford, train station, beaches, restaurants, and shopping. 15 minutes to Yale and famous New Haven landmarks. Walking distance to local restaurants, beaches, and an ocean-side playground. Public Beach: 7 minute walk - 0.4 mi Restaurants: 6 minute walk - 0.3 mi Playground: 2 minute walk - 250' *NO SMOKING*

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.

4.97 out of 5 average rating, 263 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!

A bright living area features large glass doors that open to a beautiful view of the ocean. Comfortable seating includes a sectional sofa and accent chairs, with a modern TV and light wood flooring adding to the ambiance. An umbrella provides shade for outdoor seating on the deck.

4.95 out of 5 average rating, 63 reviews

Charming 3 bedroom Beach Front Cottage

there is still time to enjoy the summer, the solitude of the beach as the tide ebbs and flows on warm days and cool nights. Have fun with the whole family, friends or loved ones at our beach front escape. Perfect for some fun in the sun. An amazing Sandbar at low-tide, a deck to relax on and a cozy inside are just a few of our great amenities. There is also a Kayak, Paddle-board and raft to enjoy. Feel free to use the fire-pit or fish off the beach. The opportunities are endless.

A comfortable living area features a plush sectional sofa with neutral cushions, arranged around a round wicker coffee table. Natural light fills the space, highlighting the light wood flooring and a serene coastal-themed artwork on the wall. Two stylish light fixtures add an elegant touch.

5 out of 5 average rating, 58 reviews

Luxe cozy 2br/1ba Milford bungalow-walk to beach!

Beautifully updated bungalow 3 minute walk to beach. Features two decks for views & enjoyment of Silver Sands State Park. Back deck has dining table & grill for dinners, drinks, birdwatching, stargazing. House has cedar outdoor shower, two double kayaks, stand up paddle board, paddles, beach chairs/towels, umbrellas, cooler, wagon. Spacious living room has tons of natural light. Bedrooms are cozy each with a full bed; primary opens to back deck. 5 min drive to downtown Milford.

The living room features a modern design with a curved green and orange sofa surrounding a light wood coffee table. A striking black fireplace provides a focal point against a light wall. A statue and decorative elements contribute to the welcoming ambience.

4.84 out of 5 average rating, 141 reviews

Westshore Luxury

Relax in the cozy living spaces, unwind in the bonus room, or take a peaceful stroll along the sandy beach just steps from your door. Enjoy breathtaking sunrises and sunsets over the water, fall asleep to the soothing sound of waves, or explore the scenic shoreline by bike. Whether you’re visiting for a quiet weekend escape or a longer stay, this charming beach home offers the perfect balance of comfort and tranquility. Quiet home for rest and relaxation — no parties or events.

Popular amenities for Milford house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.82 out of 5 average rating, 17 reviews

An inviting living area showcases a cozy green sofa and two light-colored armchairs, emphasizing a natural wood coffee table. A rustic stone fireplace adds warmth, with a well-equipped kitchen visible in the background, featuring a gray island with seating and stainless steel appliances.

Home in Brookfield

3.5 Acres of Relaxation, Pool, & Cozy Charm

4.7 out of 5 average rating, 10 reviews

The entryway is illuminated by three pendant lights, leading to an expansive outdoor view through double doors. A patterned tile floor contrasts with wood trim and walls, while potted plants and flowers add a touch of nature to the welcoming space.

Home in Oxford

Gorgeous Luxury INDOOR POOL home

5 out of 5 average rating, 28 reviews

A view through large windows, showcasing a serene lake surrounded by lush greenery. Outdoor seating is provided on the porch, inviting relaxation. The wooden ceiling complements the bright surroundings, enhancing the connection between indoor comforts and the tranquil lakefront landscape.

Home in New Milford

Bluewater Lodge at Candlewood Lake

4.95 out of 5 average rating, 266 reviews

A spacious outdoor pool is surrounded by natural greenery, featuring a stone patio and a diving board. A covered lounge area with large windows overlooks the pool, providing a serene setting for relaxation and leisure.

Home in Stamford

Midcentury Modern ZenHouse Sculptor Studio

4.8 out of 5 average rating, 30 reviews

Home in New Milford

Hidden gem steps to town w/ pool/deck/grill/sonos

4.77 out of 5 average rating, 13 reviews

A modern home is situated near a seasonal heated pool, surrounded by lush greenery. The pool features a clean, simple design with stone decking, while the house reflects contemporary architecture with large windows allowing natural light. The scenic setting offers a peaceful atmosphere.

Home in Pound Ridge

Secluded Modern Getaway-Seasonal heated pool

4.86 out of 5 average rating, 21 reviews

Home in Redding

Meeker Hill House - Country Escape w/ Heated Pool

A circular arrangement of six red outdoor chairs is positioned on a grassy area, facing the tranquil bay. The scene is enhanced by a pastel sunset sky, creating a serene ambiance. A house is visible in the background, with large windows reflecting the natural light.

4.8 out of 5 average rating, 219 reviews

Beautiful Bayfront Home • Heated Pool & Jacuzzi

Weekly house rentals

4.8 out of 5 average rating, 30 reviews

A spacious balcony features comfortable seating and a spiral staircase leading to the rooftop. The sandy beach extends towards the calm water, with a gentle curve in the shoreline visible. The horizon showcases clear blue skies, creating a serene coastal atmosphere.

Home in Fairfield

Spectacular direct waterfront w/ rooftop hot tub

4.98 out of 5 average rating, 61 reviews

Home in Trumbull

The Elijah Sterling House

An evening seascape features a shoreline dotted with smooth stones, gently reflecting hues of orange and gold from the sunset. In the distance, a silhouette of trees can be seen against the glowing horizon, blending seamlessly with the tranquil water.

5 out of 5 average rating, 10 reviews

Oceanfront Escape for 10, Steps from Sandy Beach!

5 out of 5 average rating, 15 reviews

Home in Guilford

Guilford Field House

The view showcases an open living space with light wood flooring. A cozy seating area is visible, featuring a beige sofa and a coffee table. Bright sunlight filters through open doors, illuminating the dining area and kitchen beyond, enhancing the spaciousness of the home.

4.98 out of 5 average rating, 44 reviews

La Sirena Beach Cottage in private Bayview Beach

A modern living and dining area is depicted, featuring a wooden dining table surrounded by black chairs. A cozy sofa is situated nearby, with natural light filtering through the windows. Greenery is present on a side table, enhancing the space's fresh feel.

4.95 out of 5 average rating, 57 reviews

Steps from the water!

A three-story beach house features a light-colored exterior with multiple large windows and a covered balcony on the top floor. The architectural design showcases clean lines and a welcoming entrance with a front porch. Nearby trees add a touch of greenery to the setting.

4.91 out of 5 average rating, 22 reviews

Tranquil beach retreat

An aerial view captures a beachside neighborhood, featuring a cluster of charming cottages and houses lined along the shore. The sandy beach is visible in the background, while a grassy backyard and a circular patio area are highlighted in the foreground.

4.93 out of 5 average rating, 57 reviews

The Seashell House

Private house rentals

4.92 out of 5 average rating, 36 reviews

A charming two-story farmhouse is depicted with a white exterior and a brown-shingled roof. The front porch is furnished with two chairs and includes a decorative lantern. Lush green grass surrounds the house, providing a serene setting amidst the trees.

Home in North Branford

The Gait House at High Gait Farm

A charming two-story white house features a pointed turret and an inviting front porch with a railing. The porch wraps around the sides, providing ample outdoor space. A well-maintained lawn with decorative shrubs is visible in front, and clear blue skies create a cheerful atmosphere.

4.89 out of 5 average rating, 63 reviews

The Seabreeze

5 out of 5 average rating, 35 reviews

Private 1-Bdrm Apt in West Haven

4.86 out of 5 average rating, 7 reviews

Modern Beach Home - Waterview, Close to Everything

4.93 out of 5 average rating, 55 reviews

Home in East Haven

Private Entire Home • Close to New Haven & Shore

A sandy beach is depicted with a wooden walkway leading towards the shoreline. An umbrella provides shade for beachgoers, while gentle waves are visible in the distance. A pier extends into the water, contributing to the serene coastal setting.

4.94 out of 5 average rating, 63 reviews

Adorable Walnut Beach Cottage.

4.96 out of 5 average rating, 68 reviews

A two-story house with gray siding and a bright orange front door is framed by well-maintained landscaping. A lamp post stands near the entrance, adding charm to the welcoming facade. The driveway allows for easy access, leading to a garage on the left.

Home in Trumbull

Cozy, updated single family in Fairfield County

A spacious backyard is enclosed by a wooden fence, featuring well-maintained green grass. A patio area is furnished with a dining table and an umbrella, surrounded by comfortable seating arrangements. An outdoor grill is positioned nearby, creating an inviting area for gatherings.