Vacation rentals in Milford

4.95 out of 5 average rating, 164 reviews

A serene view of the shoreline at dusk, showcasing gentle waves lapping against the sandy beach. A wooden railing leads down the steps to the water's edge, with smooth stones lining the path. A remote island can be seen in the distance, against a softly colored sky.

Apartment in Milford

The Boathouse, private downtown Harborside suite

The Boathouse is a detached one bedroom studio apartment situated behind our home in the heart of Historic downtown Milford. Through a private entrance you will discover a thoughtfully furnished bedroom (queen bed & pull out couch), dining room, full kitchen & bath. It is ideally suited for a couple/small family looking for a memorable beachtown getaway. Walk, rent bikes/kayaks, shop, dine, enjoy art, music, or a day at the beach… our quintessential New England seaside town is sure to charm you!

4.97 out of 5 average rating, 580 reviews

Apartment in Woodmont

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, 107 reviews

A functional laundry area is showcased, featuring a washer and dryer side by side. The space is well-organized, with a metal shelving unit positioned above, storing cleaning supplies. Exposed utility lines and concrete walls provide a utilitarian background, contributing to the overall practicality of the area.

Apartment in Milford

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.

Superhost

A private backyard area is seen, featuring a gravel patio with a gazebo, seating, and a picnic table. A grill is positioned nearby, and a fence encloses the space. Lush green grass borders the patio, complemented by a clear blue sky scattered with clouds.

Guesthouse in Milford

4.92 out of 5 average rating, 206 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

4.94 out of 5 average rating, 145 reviews

A serene view is captured through a large window, framing a tranquil lake surrounded by lush greenery. A potted plant is positioned in the foreground, while a wooden chair sits on the patio outside. Soft curtains drape, accentuating the bright, sunny atmosphere.

Loft in Woodmont

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.

4.95 out of 5 average rating, 106 reviews

A long wooden boardwalk winds gently towards the horizon, flanked by a railing that provides a clear view of the serene beach and distant island. The bright blue sky, dotted with wispy clouds, enhances the coastal atmosphere of the setting.

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!

The open living area showcases a modern kitchen with a central island and several bar stools. Sunlight streams through large glass doors, highlighting the neutral tones of the furnishings and the expansive water view. Wood detailing adds warmth to the atmosphere.

4.96 out of 5 average rating, 225 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!

4.99 out of 5 average rating, 114 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

4.97 out of 5 average rating, 144 reviews

A serene outdoor setting features several Adirondack chairs arranged around a fire pit, surrounded by lush green trees and natural rock formations. The calm river flows gently nearby, with sunlight filtering through the canopy, creating a peaceful retreat 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

5 out of 5 average rating, 106 reviews

Steps2Beach, Fish Pond w/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, 326 reviews

The kitchen features modern stainless steel appliances, including a gas stove and dishwasher. Natural light fills the space through a window above the sink. White cabinetry and a light countertop contrast with warm wooden flooring, creating a bright and functional cooking area.

Cottage in Milford

Summer 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.

4.99 out of 5 average rating, 127 reviews

Cottage in Milford

3 BD Cottage Walk 2 Beach + Tyde Venue w/ Fire Pit

Steps from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom, 1-bath beach cottage in the heart of Walnut Beach. Perfect for family vacations, wedding guests, or Yale visitors, our modern farmhouse-style home features a full kitchen, a private backyard with a fire pit, and peaceful coastal vibes. Walk to the sand, celebrate at Tyde, enjoy coffee on the porch, and end the day by the fire. Comfort, style, and location — all in one unforgettable stay!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Milford vacation rentals

Self check-in

Pet friendly

Laptop-friendly workspace

Monthly stays

Gym

Pet-friendly vacation rentals in Milford

4.95 out of 5 average rating, 151 reviews

An outdoor patio area features a gas fire pit surrounded by several wooden chairs. A large dining table with an umbrella is set for outdoor meals. A cozy seating area is highlighted by a light-colored sofa, offering a relaxed space for gatherings.

Home in Fairfield

Top Rated Gem | Fire Pit | Near Beach, FFU & SHU

4.93 out of 5 average rating, 256 reviews

A two-story home is nestled among trees, featuring light-colored siding and a gray roof. A red patio umbrella provides shade over a seating area in the yard, while a gravel pathway leads to the front door, enhancing the natural surroundings.

Cottage in Newtown

Private and Serene home close to I-84 and shopping

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, 103 reviews

Milford Beach House - Newer Construction!

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, 270 reviews

Sunny Westport Studio Apt. Above Historic Mill

4.95 out of 5 average rating, 115 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 New Haven

Beach Haven - waterfront, near Yale, sunsets

4.9 out of 5 average rating, 113 reviews

The entrance features a charming porch framed by white railings, with potted plants adding greenery. A welcoming front door is accentuated by patriotic decorations, and a small seating area is visible beside lush greenery and a well-maintained lawn.

Home in Fairfield

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking

4.98 out of 5 average rating, 133 reviews

The exterior view showcases a charming home surrounded by tall trees and autumn foliage. A circular wooden deck encircles a hot tub, providing an inviting outdoor space. The covered pergola offers shade, while bright flowers add color to the landscaped area.

Villa in Westville

Cozy Retreat w/ Hot Tub Near Downtown

Superhost

A spacious living area is illuminated by natural light streaming through large windows. A comfortable gray sofa with decorative pillows faces a modern coffee table. A stylish area rug adds color, while a wall-mounted TV and decorative plants enhance the space.

Apartment in New Haven

4.95 out of 5 average rating, 374 reviews

Luxury Apt with Parking and Gym | Downtown at Yale

Show all

Boutique hotels in Milford

A welcoming porch is framed by lush greenery, featuring a wooden bench adorned with colorful patterned cushions. Hanging planters add a touch of vibrancy, while the stone foundation complements the white railing and columns of the house.

5 out of 5 average rating, 4 reviews

The West Lane Inn - Deluxe Fireplace King

A fire pit is situated on a patio overlooking the water, with warm flames visible through a metal mesh. A serene sunset casts soft colours across the sky, while the bay reflects the fading light, creating a peaceful atmosphere.

Hotel room in North Fork

Aqua - Rooftop Suite

A sandy beach area is lined with several lounge chairs and umbrellas, facing the water. In the background, a building with large windows is visible, reflecting the sky and surrounding nature.

Hotel room in North Fork

AQUA BEECH HOTEL - Grand Deluxe King Suite

A modern bathroom features a marble countertop with a dark wooden vanity and a large mirror. A glass-enclosed shower with white tiles includes multiple shower heads and conveniently placed toiletries. The floor is finished with a mosaic pattern, enhancing the clean and stylish design.

4.67 out of 5 average rating, 6 reviews

The West Lane Inn - King Room

The bathroom features a granite countertop with an integrated sink. Personal care items are arranged neatly beside decorative soaps and towels. A large mirror is mounted above the sink, and additional amenities like a hairdryer are located on the wall. Natural light brightens the space.

Hotel room in Norwalk

4.33 out of 5 average rating, 12 reviews

Private king hotel room

The guest room features two spacious beds with soft bedding, complemented by a modern light fixture above. A decorative chair is positioned beside a nightstand. Natural light enters through a window, illuminating the neutral-toned walls and carpet.

5 out of 5 average rating, 5 reviews

The West Lane Inn - Double Queen Room

A serene outdoor lounge area features white woven seating and soft cushions placed on a wooden deck. The setting overlooks a calm bay with a clear blue sky, while shade structures and decorative poufs add a stylish touch to the inviting space.

Hotel room in North Fork

4.82 out of 5 average rating, 33 reviews

Aqua - Deluxe King Water View

An elegant white inn is showcased surrounded by a lush green lawn, framed by trees and flower beds. The iconic sign displays 'The West Lane Inn Boutique Hotel.' A spacious porch with white railings is visible, inviting guests to relax in a serene outdoor setting.

The West Lane Inn - Queen Room

Show all

Other great vacation rentals in Milford

5 out of 5 average rating, 31 reviews

Bull Shark Bungalow-Walk to Beach, Pet Friendly

A modern kitchen countertop is displayed, featuring a coffee maker, a sink, and a toaster. An open drawer reveals an array of coffee pods in organized sections alongside a small basket for condiments.

5 out of 5 average rating, 96 reviews

HGTV renovation! Steps to shops & water | Firepit!

The spacious living area features light oak flooring and large windows that allow natural light to fill the space. A modern sectional sofa is positioned around a central coffee table, with a cozy fireplace visible in the background. Elegant dining furniture enhances the inviting atmosphere.

5 out of 5 average rating, 9 reviews

New build! 1 house from beach

5 out of 5 average rating, 99 reviews

An oceanfront space features a kayak positioned on the floor, with sunlight illuminating the area. The backdrop showcases expansive views of the water and sky, complemented by picnic tables set outside, visible through large windows. Stairs lead to an upper level, enhancing accessibility.

Home in Woodmont

Oceanfront Retreat: Modern Beach House

4.88 out of 5 average rating, 147 reviews

A telescope is positioned on a tripod near a row of three windows, offering views of the serene waters of Long Island Sound. Light streams in, highlighting a wooden table and a striped armchair in the cozy seating area.

Cottage in Woodmont

Waterfront Beach Cottage

A spacious living area features a modern kitchen with stainless steel appliances and a large island paired with four metal bar stools. A comfortable dark sectional sofa faces a wall-mounted flat-screen television above a contemporary fireplace. Natural light floods in through wide windows offering views of the outdoors.

4.97 out of 5 average rating, 37 reviews

Modern Beach Mood!

4.99 out of 5 average rating, 76 reviews

Home in Woodmont

Seaside Cottage: water views, walk to beaches!