Vacation rentals in Milford

4.97 out of 5 average rating, 148 reviews

An outdoor dining table is set along the waterfront, featuring six black chairs and a dark umbrella. The table displays plates and glasses, with a picturesque sunset reflecting on the calm water, creating an inviting atmosphere for oceanfront dining.

Home in East Haven

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

4.93 out of 5 average rating, 268 reviews

A scenic beach scene captures individuals enjoying a relaxing day by the water. Sun loungers are positioned in the soft sand, with gentle waves lapping at the shore and a vibrant blue sky filled with fluffy white clouds.

Cottage in Guilford

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

4.95 out of 5 average rating, 103 reviews

Rows of lush green grapevines stretch along a wide pathway, leading toward the horizon under a clear blue sky. The vibrant greenery on either side frames the pathway, creating a peaceful atmosphere ideal for leisurely strolls.

Home in North Fork

Walk to Vineyards, Beach, Restaurants • Sleeps 8

• Spacious 3 BR house in heart of Jamesport - includes King, Queen & 2 twin beds. Queen air mattress also available. • Great for family vacations, weekend getaways & local weddings. • Clean sheets, pillows, fresh towels & toiletries. • Backyard complete w/ outdoor bbq, fire pit, hammock & patio seating. • Cook in open kitchen fully equipped w/ dishes, utensils, spices, pots & pans; eat local ingredients from nearby farms & markets. • Indoor & outdoor dining tables seat up to 8 guests.

4.92 out of 5 average rating, 205 reviews

A wide-angle view captures the beach and waterfront community, showcasing houses lined along the shore. A sandy beach meets calm waters, with a jetty extending into the sea. Fluffy clouds float in a clear blue sky above the scenic landscape.

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.

4.96 out of 5 average rating, 212 reviews

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

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!

5 out of 5 average rating, 103 reviews

A cozy cabin nestled among trees is shown at dusk, with warm light streaming from the windows. An outdoor fire pit is visible, adding an inviting glow to the natural surroundings. Tall trees frame the scene, enhancing the tranquil atmosphere.

Cottage in South Salem

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

4.88 out of 5 average rating, 188 reviews

Home in New Milford

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

5 out of 5 average rating, 102 reviews

A well-lit wooden deck features comfortable seating arrangements with padded chairs, perfect for relaxation. Soft lights illuminate the space, creating a welcoming atmosphere. A protective railing borders the deck, with a view of a privacy fence in the background.

Home in Milford

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!

4.9 out of 5 average rating, 100 reviews

A charming building is illuminated by soft evening light, surrounded by blossoming trees adorned with twinkling lights. Outdoor seating is visible, inviting guests to enjoy the vibrant atmosphere of the town. The sky transitions to a serene twilight blue, enhancing the scene.

Guest suite in Branford

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

4.97 out of 5 average rating, 119 reviews

Cottage in Fairfield

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

4.92 out of 5 average rating, 117 reviews

Home in New Fairfield

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

4.84 out of 5 average rating, 154 reviews

The approach to the house features a stone pathway leading up to a front porch, flanked by neatly arranged flower planters. The well-maintained lawn provides an inviting green backdrop. Steps lead up to the entrance, with a decorative light fixture positioned along the pathway.

Home in Stamford

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

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

4.97 out of 5 average rating, 151 reviews

An airy living room features white walls and a light wood ceiling, enhancing the spacious feel. A comfortable white sofa is paired with a round coffee table. Large glass doors offer unobstructed views of the water and access to the outdoor deck, merging indoor and outdoor living.

Cottage in North Fork

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

4.89 out of 5 average rating, 486 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

4.95 out of 5 average rating, 317 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

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

4.92 out of 5 average rating, 119 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

4.94 out of 5 average rating, 413 reviews

A spacious living area features a dark sofa and a patterned armchair, offering comfortable seating. A wooden Murphy bed is folded against the wall, while a small table with a lamp and decorative flowers adds to the inviting ambiance. Large windows provide natural light.

Guest suite in Fairfield

Private Studio Apartment; Kitchen; Fully Furnished

4.94 out of 5 average rating, 174 reviews

A private hot tub is situated under a gazebo with string lights, surrounded by vibrant pink azalea flowers. The outdoor space features a cozy seating area, a propane grill, and a glimpse of the home's exterior in the background.

Home in Stratford

Cozy Colonial - Private Hot Tub & Entire House

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House rentals in Milford

5 out of 5 average rating, 133 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

4.98 out of 5 average rating, 57 reviews

A charming exterior of a home is framed by lush greenery and trees. A stone pathway leads to a welcoming staircase, adorned with a flower box underneath the window. Soft sunlight filters through the leaves, creating a serene atmosphere.

Home in Cos Cob

Cos Cob CT, 3bdrm, 2bath, with workout room

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

4.76 out of 5 average rating, 106 reviews

A modern kitchen displays sleek white cabinetry and a spacious island with four metal stools positioned around it. Stainless steel appliances include a refrigerator and oven, and light-colored tile flooring enhances the open layout. A window is partially visible in the background.

Home in New Haven

Heavenly Home in New Haven /5 mins drive from Yale

5 out of 5 average rating, 7 reviews

A spacious living area is highlighted by a dark sectional sofa and a comfortable lounge chair. The wooden wall adds texture, while natural light enters through two windows, dressed in simple curtains. A light wood TV stand and a side table complement the setting.

Home in West Haven

Cozy cape cod

4.8 out of 5 average rating, 101 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

5 out of 5 average rating, 16 reviews

A spacious living area is furnished with a large sectional sofa adorned with decorative throw pillows. A coffee table sits centrally on a patterned area rug, complemented by artwork on the walls and natural light filtering through the windows.

Home in Cos Cob

GREENWICH HOUSE WITH NYC FLAIR/CLOSE TO BEACH /NYC

5 out of 5 average rating, 14 reviews

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.

Home in Milford

Beach Neighborhood House

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Pet-friendly house rentals Milford

4.86 out of 5 average rating, 7 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, 501 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

4.9 out of 5 average rating, 21 reviews

A charming blue Cape-style house is framed by green grass and tall trees. The entrance features a red door surrounded by large windows, while landscaped areas with small shrubs enhance the welcoming appearance. A gravel driveway leads to the property, providing easy access.

Home in Southbury

Cozy Family and Pet friendly 3 br Home

4.97 out of 5 average rating, 88 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

4.8 out of 5 average rating, 103 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, 32 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