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Vacation rentals in Milford

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Top-rated vacation rentals in Milford

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

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

4.94 out of 5 average rating, 163 reviews

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!

Top guest favorite

Apartment in Woodmont

4.97 out of 5 average rating, 580 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!

Top guest favorite

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

4.98 out of 5 average rating, 106 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.

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.

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

4.94 out of 5 average rating, 144 reviews

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.

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

4.95 out of 5 average rating, 105 reviews

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.

Home in Milford

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!

Top guest favorite

Home in Milford

4.99 out of 5 average rating, 113 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

Top guest favorite

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

4.97 out of 5 average rating, 143 reviews

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

Top guest favorite

Home in Milford

5 out of 5 average rating, 105 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!

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

4.95 out of 5 average rating, 326 reviews

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.

Top guest favorite

Cottage in Milford

4.99 out of 5 average rating, 127 reviews

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

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Houses

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Hotels

Stylish accommodations and amenities

Popular amenities for Milford vacation rentals

Laptop-friendly workspace

Pet-friendly vacation rentals in Milford

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

4.96 out of 5 average rating, 150 reviews

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

A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.

Home in East Haddam

4.94 out of 5 average rating, 224 reviews

Romantic Getaway at The Lake!

Top guest favorite

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.

Home in Milford

5 out of 5 average rating, 103 reviews

Milford Beach House - Newer Construction!

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.

Place to stay in Southport

4.94 out of 5 average rating, 270 reviews

Sunny Westport Studio Apt. Above Historic Mill

A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.

Home in Southampton

4.96 out of 5 average rating, 171 reviews

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

Top guest favorite

The kitchen features modern gray cabinetry with ample counter space. Stainless steel appliances, including a refrigerator and dishwasher, are visible. A large window allows natural light to fill the room. A dining area with a table and chairs is situated nearby.

Home in Fairfield

5 out of 5 average rating, 109 reviews

Peaceful Suburban Colonial w/New Kitchen.

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, 373 reviews

Luxury Apt with Parking and Gym | Downtown at Yale

Top guest favorite

A modern white structure with large windows is surrounded by lush greenery, including a prominent tree and shrubs. A small seating area with a table and chairs is visible in the gravel courtyard, providing a tranquil outdoor setting embraced by nature.

Guesthouse in Southport

4.96 out of 5 average rating, 194 reviews

Southport, CT across from BEACH

Boutique hotels in Milford

A collection of potted plants is displayed on a textured surface. Various pots in earthy tones and styles, including a green-speckled pot, terracotta pots, and a light-colored container, house a diversity of succulents and cacti, adding a touch of nature to the interior.

Hotel room in North Fork

Luxury Lifestyle Hotel, Greenport Village, NY

An outdoor area features well-maintained green grass leading to a calm bay view. Lounge chairs and picnic tables are arranged throughout, with palm trees and other greenery. Tents and shaded seating areas are present, with sunlight creating a bright atmosphere across the landscape.

Hotel room in North Fork

5 out of 5 average rating, 4 reviews

Aqua - Rooftop Suite

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

A spacious communal area features a long, dark wooden table surrounded by benches. A rustic stone fireplace is situated against a teal accent wall, with decorative shelves displaying various items. Soft lighting creates a calm ambiance throughout the room.

Hotel room in North Fork

4.66 out of 5 average rating, 133 reviews

The Lin Beach House -- Edie's 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.

Hotel room in Ridgefield

5 out of 5 average rating, 5 reviews

The West Lane Inn - Double Queen Room

An open entryway features polished marble flooring and soft-colored walls. A grand staircase with wooden handrails leads to the upper level. Various decorative elements, including mirrors and vintage furnishings, enhance the inviting ambiance of the welcoming space.

Hotel room in North Fork

4.6 out of 5 average rating, 149 reviews

The Lin Beach House -- Bianca Suite

The exterior of the hotel features a manicured lawn with colorful flower beds, including vibrant red roses. Wooden benches are positioned along the pathways leading to the guest rooms, which are framed by well-maintained landscaping and large windows that invite natural light.

Hotel room in Southampton

4.75 out of 5 average rating, 99 reviews

Somewhere in the Hamptons

A spacious communal area features a long, dark wooden table surrounded by benches. A brick fireplace is adorned with decorative items, and soft lighting casts a warm glow across the room. Large windows allow natural light to fill the space, enhancing its welcoming ambiance.

Hotel room in North Fork

4.74 out of 5 average rating, 135 reviews

The Lin Beach House -- Lillian's Suite

Other great vacation rentals in Milford

Apartment in Milford

4.91 out of 5 average rating, 11 reviews

September & Shoulder season at the Seashore in CT!

Top guest favorite

Home in Milford

5 out of 5 average rating, 31 reviews

Bull Shark Bungalow-Walk to Beach, Pet Friendly

Top guest favorite

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.

Home in Milford

5 out of 5 average rating, 94 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.

Home in Milford

5 out of 5 average rating, 9 reviews

New build! 1 house from beach

Top guest favorite

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

5 out of 5 average rating, 98 reviews

Oceanfront Retreat: Modern Beach House

Top guest favorite

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.

Home in Milford

4.97 out of 5 average rating, 37 reviews

Modern Beach Mood!

Top guest favorite

Home in Woodmont

4.99 out of 5 average rating, 76 reviews

Seaside Cottage: water views, walk to beaches!

A shaded porch is visible, featuring a round table with a floral tablecloth and several chairs. The tranquil ocean is seen in the background, while distant land can be discerned on the horizon. Soft light illuminates the space, enhancing the inviting setting.

Home in Woodmont

4.96 out of 5 average rating, 47 reviews

Beachfront paradise- come, stay, relax!

Quick stats about vacation rentals in Milford

Total rentals
260 properties
Total number of reviews
11K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
150 properties have a dedicated workspace

Frequently Asked Questions

Where should I stay in Milford?
Make yourself at home in Milford by choosing from our most frequently booked neighborhoods. We have over 30 vacation rentals in Putney, and over 130 vacation rentals in Parkway - Wheelers Farm Road.
Are there vacation rentals with a dedicated workspace in Milford?
Yes! Work meets play with ease at over 150 vacation rentals in Milford featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Milford?
Experience the best of Milford with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Milford?
Four-legged friends are welcome in Milford. Choose from more than 100 vacation rentals for guests traveling with pets.
Do cottage rentals in Milford have self check-in?
Absolutely! We offer over 10 cottage rentals with self check-in in Milford. Enjoy a tailored experience with all the comforts you desire.
Are there Milford vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Milford, available on Airbnb. Make a splash and soak up the sun in style!

Destinations to explore