Pet-friendly holiday rentals in Milford

4.93 out of 5 average rating, 359 reviews

A white Dutch door is framed by rustic wooden walls, showcasing a combination of horizontal and vertical planks. A small lantern hangs nearby, and a woven basket adorns the wall beside the door. A simple bench with a patterned cushion sits on the side.

Guest house in Southbury

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

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.

A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.

4.99 out of 5 average rating, 141 reviews

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

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, 143 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!

5 out of 5 average rating, 123 reviews

HGTV reno! Fall Foliage, near New Haven, Firepit!

*Inquire now monthly discount Jan* *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 speeds

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!

4.95 out of 5 average rating, 357 reviews

A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.

Cottage in Milford

Fall Sale! CozyCottage/Pet-friendly/Walk to Beach

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

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, 119 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.

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.

4.95 out of 5 average rating, 119 reviews

An outdoor seating area is presented with a comfortable couch adorned with colorful throw pillows. A small table features a decorative item, while a vibrant side table adds a pop of color. A patterned rug complements the space, surrounded by greenery.

Flat in Milford

Downtown, Private balcony, 1gb fiber Wi-Fi

Charming 2nd floor one bedroom apartment with a separate entrance located in Milford's Historic district south of the green. You'll be 0.4 miles to the Milford train station. It's only 0.3 miles to the Milford Green which features restaurants, nightlife, and the Milford Harbor. Three local breweries are within 20 minutes of driving. Enjoy 17 miles of coastline where you can swim, kayak, and paddle board. Check in time is flexible with self check in lockbox.

A cozy living room features a comfortable sofa adorned with decorative pillows, a wooden rocking chair, and a coffee table with a bowl. A wooden entertainment unit holds a television, while wooden flooring leads to a staircase and an adjoining room filled with natural light.

4.85 out of 5 average rating, 112 reviews

Cozy Colonial Style House in Beach Town

Charming home in calm New England neighborhood. Well connected: 20 mins to New Haven, 90 mins to New York, 2.5h to Boston. Colonial style with beautiful hardwood floors, lots of outside seating space on front and back porch. Back yard dining table and private driveway for 2-3 cars. A few minutes from Walnut Beach and Silver Sands State park as well as forest trails. Within walking distance from a brewery, restaurants, and a playground.

Place to stay in Southport

An open studio space is highlighted by original wooden beams and warm, polished hardwood floors. Multiple skylights provide ample natural light. Furnishings include a comfortable couch, a coffee table, and storage units adorned with artwork, creating a charming, functional atmosphere.

4.94 out of 5 average rating, 279 reviews

Sunny Westport Studio Apt. Above Historic Mill

Historic Charm Meets Modern Comfort: A Unique Studio Retreat Perched atop a restored 19th-century Cider Mill, this sunlit studio blends timeless character with modern amenities. Enjoy stunning views of a picturesque stream, serene meadows, and diverse wildlife. Just moments from Southport Village, yet offering a peaceful escape, it's perfect for history lovers, business travelers, and design enthusiasts seeking a unique getaway.

Popular amenities for Milford pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

An aerial view showcases a beach community with a stretch of sandy shoreline. The buildings are seen along the coast, with clusters of homes and shops in proximity. A clear blue sky and calm water complement the scenic landscape.

4.9 out of 5 average rating, 61 reviews

Bobby's Beach Bungalow

4.98 out of 5 average rating, 65 reviews

A bright kitchen area is featured, equipped with modern appliances and a white countertop. A cozy seating area includes a navy sofa adorned with pink cushions against a wood-paneled accent wall. Decorative plants and a vase with blue flowers add a fresh touch to the space.

Home in Fairfield Beach

5 Minute Walk to Beach & Downtown Fairfield

4.85 out of 5 average rating, 102 reviews

A quaint two-story home is set within a serene neighborhood, featuring a mix of stone and siding exteriors. Lush greenery lines the property, and a small shed is visible on the side. The front yard is well-maintained, providing a welcoming appearance.

Home in East Shore

Rudy2

A spacious living room features a large sectional couch facing an 85-inch TV. Natural light fills the area through multiple windows, complemented by soft gray walls and a ceiling fan. A unique shark decor piece hangs above, with a glimpse of the outdoor area visible through sliding doors.

5 out of 5 average rating, 44 reviews

Bull Shark Bungalow-Walk to Beach, Pet Friendly

4.92 out of 5 average rating, 93 reviews

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.

Home in West Haven

Westshore Luxury

The three-story house features a light grey exterior with multiple balconies on the front. A double garage is located on the ground floor, with large windows above offering a view of the spacious balconies. The welcoming entrance is framed by well-maintained landscaping.

5 out of 5 average rating, 14 reviews

New build! 1 house from beach

The exterior of a charming beach house is presented, featuring a light-colored facade with a combination of siding and shingles. A welcoming front porch is visible, surrounded by a well-kept lawn and a walkable pathway leading to the entrance.

4.95 out of 5 average rating, 40 reviews

Cozy Milford Beach House

5 out of 5 average rating, 13 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

Pet-friendly home rentals with a pool

5 out of 5 average rating, 16 reviews

Home in Weston

Dream Home w/ Pool & Basketball Court on 3 Acres

5 out of 5 average rating, 31 reviews

Home in Redding

Country Retreat | Fire Pit | BBQ

4.92 out of 5 average rating, 59 reviews

A bright sleeping area features a spacious bed adorned with various pillows in shades of gray and white. Two table lamps flank the bed, providing soft illumination. The warm wall color enhances the cozy ambiance of the room.

Flat in Trumbull

Cozy studio unit

A serene view of the Long Island Sound is captured at sunset, featuring soft pastel hues in the sky. A few clouds are present, and the gentle water surface reflects the vibrant colors. A flagpole with an American flag stands prominently in the foreground.

4.83 out of 5 average rating, 106 reviews

Spacious 4 bedroom, oasis with ocean views galore

4.98 out of 5 average rating, 105 reviews

A spacious loft area features high ceilings with exposed beams and warm wooden accents. Two comfortable leather sofas face a central ottoman, surrounded by artwork and decor. Natural light floods in through large windows, highlighting the rich wooden floors and a decorative rug.

Cottage in Black Rock

Spacious Cottage Loft

4.79 out of 5 average rating, 29 reviews

A rustic cabin with a distinctive thatched roof is set among lush greenery. The natural stone steps lead to the entrance, and a wooden gate adorned with climbing vines is slightly ajar, inviting guests to explore the serene surroundings.

Home in Ridgefield

Log House, sits on 3acres. A retired mini farm.

5 out of 5 average rating, 39 reviews

A coastal home with a light wood exterior is set on pilings, resting above a rocky shoreline. Floor-to-ceiling windows offer expansive views. A spacious deck with a dining table is positioned prominently, inviting relaxation while overlooking the water.

Home in Madison

Waterfront Beach House with pool

4.68 out of 5 average rating, 329 reviews

A swimming pool is surrounded by a spacious wooden deck, featuring several lounge chairs and bright blue Adirondack chairs. Lush greenery and trees frame the area, providing a secluded and peaceful atmosphere.

Flat in Shelton

1ST FLR APT Your private resort, now FAMILY-ized!

Private, pet-friendly home rentals

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.

4.95 out of 5 average rating, 39 reviews

* cozy coastal fall in Milford, pet friendly

4.86 out of 5 average rating, 22 reviews

A single-story blue home is presented, featuring a combination of large windows and a welcoming front entry. Stone steps lead to the door, with landscaped rocks and greenery enhancing the outdoor space.

Home in East Haven

Private Entire Home • Close to New Haven & Shore

Guest house in Fairfield Beach

A scenic view of a calm waterway is framed by a wooden deck. Two white chairs with blue stripes are positioned for relaxation. A small table holds decorative items, while a dock extends into the water, surrounded by greenery and gentle waves.

4.97 out of 5 average rating, 32 reviews

The Creekside Cottage

5 out of 5 average rating, 16 reviews

A modern open studio features a light-colored couch adorned with green pillows, and a small coffee table in the living area. The kitchen is equipped with appliances, and natural light fills the space, highlighting the warm wood flooring.

Flat in Hamden

In-law Private Studio Apartment

5 out of 5 average rating, 26 reviews

The exterior of the modern beachside retreat is showcased, highlighting a three-story structure with balconies on the upper floors. The light-colored facade is complemented by stone accents and landscaped lawn, providing a welcoming entryway. Nearby streets and neighboring homes create a quaint coastal neighborhood ambiance.

Home in Fairfield Beach

Stareway to Heaven

4.65 out of 5 average rating, 20 reviews

A modern living area is showcased, featuring a plush blue sofa and a cozy cream armchair. A flat-screen TV is positioned on a light wooden media console. Decorative art pieces adorn the walls, with natural light filtering through the window.

Flat in Milford

Downtown Milford New,Train Access,Pets,Gym,Unit E3

4.93 out of 5 average rating, 45 reviews

The studio features a neatly arranged sleeping area with a quilted bedspread in blue and white patterns. A desk with a chair is positioned nearby, allowing for a focused workspace. Natural light streams through sheer curtains, creating a bright and welcoming ambiance.

Home in Bridgeport

Cozy Studio in Bridgeport