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Family-friendly vacation rentals in Stratford

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Stratford

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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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

4.9 out of 5 average rating, 118 reviews

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

ENTIRE 2nd FL for up to 2️⃣ adult guests ONLY 2️⃣ Rooms➕Skylit Full Bath Exclusive Driveway Parking spots➕Private Main Entrance, separate from full-time renters on 1st FL using back entries Heat & Cool: wall-mounted AC➕portable Dyson ➕ Central AC w/2 sensors - host adjustable remotely TV is Screen only, works with Bluetooth & Chromecast, NO Services Kitchenette: heat/store food (NO cooking), allows affordable stay in affluent Fairfield Town Professional Clean Service Host Assistance Virtually

Top guest favorite

A spacious studio layout includes a cozy queen bed adorned with a geometric quilt. Nearby, a comfortable seating area features a patterned sofa and a green chair. Natural light flows through large windows adorned with bamboo shades, illuminating the warm wood floor.

Apartment in Milford

4.95 out of 5 average rating, 173 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

Two colorful sailboats glide across the water, their vibrant sails displaying shades of orange, yellow, and blue. In the background, a green tree line is visible along the shore, suggesting a natural setting.

Home in Milford

4.94 out of 5 average rating, 141 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!

Top guest favorite

An aerial view captures the beachside neighborhood with the glimmering water in the background. The Tyde wedding venue is marked, along with the listing's address. Lush greenery and residential homes are visible, showcasing the proximity to the shore and nearby amenities.

Home in Milford

5 out of 5 average rating, 104 reviews

HGTV renovation! Steps to shops & water | Firepit!

*Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from a quaint downtown •1 block from the water, •Walk to the beach, restaurants, coffee house, ice cream parlor, deli, convenience store, liquor store, and more... • Complete Clean Linen Participant - luxe, white, 100% cotton sheets & fluffy duvets •Relax in the FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue!

Top guest favorite

A spacious bedroom features a king bed with a soft green duvet and decorative pillows. Two nightstands with lamps are positioned on either side. Natural light enters through two windows adorned with bamboo shades. A framed coastal artwork is displayed above the headboard.

Guest suite in Fairfield

4.94 out of 5 average rating, 168 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

Top guest favorite

A serene garden area is seen, featuring lush green grass and vibrant flowerbeds with orange blooms. A tranquil pond is visible in the background, surrounded by trees and natural landscaping, creating a peaceful outdoor setting.

Apartment in Milford

4.98 out of 5 average rating, 117 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.

The exterior of a beach cottage is shown, featuring light-colored siding and blue shutters. A white railing surrounds a small porch, leading to a front door. Lush greenery and a few decorative elements enhance the inviting appearance of the home.

Cottage in Milford

4.95 out of 5 average rating, 113 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!

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

4.96 out of 5 average rating, 232 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

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.

Home in Milford

4.99 out of 5 average rating, 124 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

An open living area is highlighted by a light grey sectional sofa positioned alongside a wooden coffee table. Above, a wooden ladder leads to a lofted space. Built-in cabinetry and a black stove offer additional functionality, while large windows provide natural light.

Cottage in Weston

4.97 out of 5 average rating, 156 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

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

4.95 out of 5 average rating, 335 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

A cozy living room is featured with a combination of a grey sofa and an orange couch. A decorative white coffee table rests on a patterned area rug, while a faux fireplace is accented by a round sunburst mirror and decorative items. Natural light enters through a nearby window.

Cottage in Milford

4.99 out of 5 average rating, 135 reviews

3BD Cottage Walk 2 Beach and Tyde Wedding Venue

Walking distance 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!

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Popular amenities for Stratford family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A light-filled entryway welcomes guests with wooden accents and a neutral color palette. A console table, adorned with decorative items, stands against the wall. The entrance features a small seating area with natural light filtering through the window, complemented by a decorative clock.

Bungalow in Plymouth

4.98 out of 5 average rating, 102 reviews

Lakefront Bungalow Bliss - 2BR Cottage

A spacious outdoor area includes a fenced saltwater pool surrounded by patio space and lounge chairs. A gazebo with seating is visible in the background, while well-maintained grass and landscaping create an inviting atmosphere. A fire pit is positioned nearby.

Guest suite in Northport

4.94 out of 5 average rating, 121 reviews

Coastal Villa Suite pool•sauna•gym•theater•beach

A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.

Home in Port Jefferson

4.8 out of 5 average rating, 340 reviews

The Hilltop Harborview

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

4.95 out of 5 average rating, 184 reviews

Luxury cottage by the sea with hot tub and pool

Cabin in New Fairfield

4.96 out of 5 average rating, 344 reviews

The Little Lake Cabin— hot tub, fire pit, & kayaks

Top guest favorite

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.

Home in Woodmont

4.96 out of 5 average rating, 105 reviews

Oceanfront Retreat: Modern Beach House

Top guest favorite

A spacious hot tub is situated on the deck, surrounded by a wooden fence for privacy. Two chairs and a small table are positioned nearby, while additional seating options are visible in the background. The setting is framed by trees, offering a natural ambiance.

Guesthouse in Guilford

4.95 out of 5 average rating, 107 reviews

Guilford Lakes Cottage, with hot tub and fire pit.

Top guest favorite

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

4.95 out of 5 average rating, 118 reviews

Beach Haven - waterfront, near Yale, sunsets

Family- and pet-friendly home rentals

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

4.94 out of 5 average rating, 339 reviews

Charming Guest Cottage with Modern Amenities

Top guest favorite

The exterior of a two-story colonial home is framed by lush greenery, presenting a manicured lawn. A charming porch with steps invites guests, while a brick chimney rises from the roof, adding character to the light-colored siding.

Guesthouse in South Salem

4.94 out of 5 average rating, 295 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A spacious bedroom features a large bed with crisp white linens, surrounded by vibrant artwork and colorful cabinetry. Warm wood paneling lines the ceiling, and two bedside lamps provide soft illumination, contributing to a bright and inviting environment.

Place to stay in Southport

4.96 out of 5 average rating, 321 reviews

Sunny Westport 2 BR Retreat above Historic Mill

A bright kitchen area features a light wooden dining table surrounded by four high-backed chairs with soft seat cushions. The sleek kitchen, equipped with modern stainless steel appliances, showcases a minimalist aesthetic, complemented by subtle gray tiles and white cabinetry.

Apartment in Downtown New Haven

4.94 out of 5 average rating, 136 reviews

DTWN | Yale | Wooster Square | Laundry | WiFi

Top guest favorite

Home in Pound Ridge

5 out of 5 average rating, 168 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Top guest favorite

A cottage nestled in a lush green setting is highlighted, surrounded by trees. The lawn is spacious and well-maintained, featuring a hammock between two trees. The structure showcases a simple facade with light blue siding, white window frames, and a chimney.

Home in Newtown

4.99 out of 5 average rating, 101 reviews

Comfortable home away from home- near everything

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, 112 reviews

Peaceful Suburban Colonial w/New Kitchen.

A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.

Guest suite in Wilton

4.79 out of 5 average rating, 207 reviews

Guest suite with private enter

Family-friendly home rentals with a pool

An indoor resistance pool is surrounded by a wooden deck, featuring calming turquoise water. Natural light floods in through large windows, while decorative sculptures and plants adorn the space, adding to the serene environment.

Guest suite in Redding

4.92 out of 5 average rating, 180 reviews

Artist Retreat in Beautiful Country Setting

Top guest favorite

A swimming pool is set in a lush green yard, surrounded by trees and flowering plants. Comfortable lounge chairs are positioned nearby, while a large rock adds a natural element to the pool area. The property's main house stands in the background, completing the inviting scene.

4.98 out of 5 average rating, 240 reviews

Escape to a Restored New England Antique Milk Barn

Top guest favorite

A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.

Guest suite in Monroe

4.97 out of 5 average rating, 206 reviews

Garden Level Suite with Beautiful Pool

Guesthouse in Easton

4.85 out of 5 average rating, 106 reviews

Entire Guest House at Fox Pond Farm.

A spacious outdoor pool is surrounded by a stone patio, nestled within a serene environment of tall trees. The pool features a diving board and is complemented by nearby planters. A main house can be seen in the background, enhancing the tranquil setting.

Home in Stamford

4.95 out of 5 average rating, 256 reviews

Midcentury Modern ZenHouse Sculptor Studio

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.

Apartment in Trumbull

4.94 out of 5 average rating, 52 reviews

Cozy studio unit

An in-ground pool is surrounded by a white picket fence, featuring a clean, inviting blue surface. Lush green trees and colorful foliage can be seen in the background, while a small shed is positioned to one side. Sunlight brightens the entire scene under a clear sky.

Home in Woodmont

4.84 out of 5 average rating, 95 reviews

Spacious 4 bedroom, oasis with ocean views galore

A spacious and inviting pool area features a large, unheated swimming pool surrounded by a stone deck. Sun loungers are positioned near the water, and lush greenery provides a natural backdrop, creating a serene outdoor environment.

Guest suite in Holmes

4.98 out of 5 average rating, 203 reviews

Prvt pool Huge, Eclectic space… 1.5 hr to NYC!

Quick stats about vacation rentals that are family-friendly in Stratford

Total rentals
110 properties
Nightly prices starting at
R528 ZAR before taxes and fees
Total number of reviews
4K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Wifi availability
110 properties include access to wifi

Destinations to explore