Vacation rentals in Milford

4.95 out of 5 average rating, 158 reviews

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!

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, 137 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!

4.97 out of 5 average rating, 574 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!

4.92 out of 5 average rating, 205 reviews

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

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, 142 reviews

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, 102 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!

A bright kitchen area showcases a round wooden dining table surrounded by black chairs. Large glass sliding doors reveal scenic water views, inviting natural light into the space. The decor includes a centerpiece vase, with woven baskets visible above the cabinets.

4.96 out of 5 average rating, 215 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, 106 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

4.96 out of 5 average rating, 131 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, 103 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, 318 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

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly

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, 122 reviews

Cottage in Milford

Walk 2 Beach + Tyde Venue |3BD Cottage 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

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Popular amenities for Milford vacation rentals

Self check-in

Pet friendly

Laptop-friendly workspace

Gym

BBQ grill

Stay near Milford's top sights

Stop & Shop4 locals recommend

Trader Joe's6 locals recommend

Stonebridge Restaurant28 locals recommend

Connecticut Post Mall17 locals recommend

The Greek Spot Cafe & Grill8 locals recommend

Scoot & Paddle13 locals recommend

Pet-friendly vacation rentals in Milford

4.92 out of 5 average rating, 245 reviews

A single-story cottage is set amidst greenery, showcasing maroon siding and multiple windows. The front yard features a manicured lawn with a few flowerbeds, and a stone pathway leads to the entrance, flanked by tall trees providing shade.

Cottage in Middlefield

Lake Beseck cottage

4.93 out of 5 average rating, 319 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.

Guesthouse in Southbury

Charming Guest Cottage with Modern Amenities

4.82 out of 5 average rating, 159 reviews

A wooden deck is surrounded by lush greenery, featuring two lounge chairs positioned for relaxation. A charming cabin stands in the background, accentuated by a mix of trees and plants that create a secluded atmosphere.

Cottage in Carmel Hamlet

Cozy Dogfriendly Cabin & Backyard on Scenic Lake.

4.99 out of 5 average rating, 138 reviews

A bright dining area features a table surrounded by six chairs, with a decorative tablecloth. High ceilings with wooden beams enhance the openness. Large windows provide natural light, and a sideboard adds functional storage. A cozy seating arrangement can be seen in the background.

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

4.89 out of 5 average rating, 487 reviews

A serene beach scene illustrates a vast stretch of shoreline, with gentle waves lapping at the sand. The water is a mix of blue and green hues under a clear sky, providing a calming seaside atmosphere.

Cabin in Rocky Point

Great little place just for a couple

4.97 out of 5 average rating, 148 reviews

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

4.95 out of 5 average rating, 103 reviews

A single-story brick house is set amidst a lush green lawn, framed by colorful flowers and bushes. A pathway leads to the front entrance, with a chimney visible on the right side. Tall trees provide shade in the background under a clear blue sky.

Home in North Fork

Walk to Vineyards, Beach, Restaurants • Sleeps 8

4.92 out of 5 average rating, 120 reviews

A bright sleeping area features a spacious bed with light blue bedding. A cozy seating area includes a gray sofa and a decorative chair beside a small coffee table. Natural light enters through a window dressed in turquoise curtains, with a television mounted on the wall.

Apartment in Middlebury

Cozy Apartment with Water View of Brook

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House rentals in Milford

4.92 out of 5 average rating, 118 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

4.89 out of 5 average rating, 104 reviews

The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.

Home in East Haven

Welcome To Piper's Rest

5 out of 5 average rating, 135 reviews

A single-story home is situated on a well-kept lawn with lush greenery and small bushes lining the front. The exterior features light-colored siding and a dark roof, complemented by multiple large windows that enhance natural light.

Home in Cheshire

Pool House

4.93 out of 5 average rating, 107 reviews

The living area features a dark grey sofa adorned with decorative pillows, positioned on a textured area rug. A small wooden side table stands next to the sofa, and a framed landscape artwork hangs on the wall. A dining area is visible through the doorway.

Home in Fairfield

Downtown Fairfield 3 bedroom Colonial

4.93 out of 5 average rating, 159 reviews

A clean and functional kitchen features white cabinetry, stainless steel appliances, and a spacious countertop. A stovetop with an exhaust hood is visible. Natural light flows in through a window above the sink, while a dining area with wooden chairs is seen in the background.

Home in Mamaroneck

3 Bed/2 Bath Private Home in Mamaroneck

4.8 out of 5 average rating, 102 reviews

A white anchor, inscribed with 'BYRAM SHORE BOAT CLUB,' is positioned prominently in a landscaped area. It is surrounded by greenery and colorful blooming flowers, set against a backdrop of finely textured gravel.

Home in Greenwich

Greenwich abode Close to Just about Everything

A charming cape-style home is presented with a well-kept front yard, featuring manicured hedges and vibrant flowering shrubs. The structure, adorned with friendly neutral tones, displays a welcoming entryway lined with planters. A concrete pathway leads to the porch, enhancing the home's inviting curb appeal.

5 out of 5 average rating, 14 reviews

Beach Neighborhood House

4.82 out of 5 average rating, 125 reviews

A welcoming living area features a comfortable gray sofa and two armchairs. A wooden coffee table sits in the center, accompanied by a decorative candle arrangement. Light-colored walls are complemented by large windows, allowing natural light to illuminate the space.

Home in Fairfield

Southport Shoreline Charm: Elegant Coastal Escape

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Pet-friendly house rentals Milford

4.88 out of 5 average rating, 8 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

4.43 out of 5 average rating, 7 reviews

A bright bedroom features a spacious bed adorned with light fabric drapery. Natural light floods in through nearby windows. A mirror stands against the wall, and a wooden nightstand complements the warm wooden flooring. A cozy rug adds texture, enhancing the inviting atmosphere.

Home in North Haven

Pet Friendly Relaxing Retreat

4.96 out of 5 average rating, 502 reviews

A flowering tree with cascading pink blooms stands in a lush green yard. The vibrant flowers contrast with the wooden exterior of the house in the background, which features large windows and a warm architectural design. The scene is well-lit, conveying a serene outdoor environment.

Home in Wading River

Your Zen Retreat

4.94 out of 5 average rating, 115 reviews

Sailboats glide across a calm blue sea, with distant shorelines visible under a clear sky. The tranquil waters reflect shades of blue, creating a serene nautical setting that accentuates the beauty of the surrounding landscape.

Home in Shippan Point

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

4.97 out of 5 average rating, 90 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

4.79 out of 5 average rating, 107 reviews

A cozy bedroom features a wooden bed with a white comforter and an array of decorative pillows. A nightstand holds a lamp, while a striped blanket is draped over a bench at the foot of the bed. Natural light brightens the space.

Home in West Haven

Cozy Home, Dog and Family Friendly - book today!

4.94 out of 5 average rating, 33 reviews

A serene backyard scene is presented, featuring a sparkling pool surrounded by gray lounge chairs. Lush green trees create a privacy barrier in the background, while a garden area and fencing add to the charm of the outdoor space.

Home in North Salem

North Salem Home with Pool & Great Yard