Family-friendly vacation rentals in Bridgeport

4.93 out of 5 average rating, 198 reviews

A spacious bedroom features a queen-sized bed with a light-colored quilt. Two elegant armchairs are positioned around a glass-topped table. Natural light floods in through multiple windows adorned with lace curtains, providing views of the verdant surroundings.

Guest suite in Fairfield

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; exclusive use of kitchen (was the main kitchen of the house); private entrance to space thru side door of the house. Two large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

KitchenFamilyWalkability

4.98 out of 5 average rating, 112 reviews

A spacious loft area features high ceilings with exposed beams and warm wooden accents. Two comfortable leather sofas face a central ottoman, surrounded by artwork and decor. Natural light floods in through large windows, highlighting the rich wooden floors and a decorative rug.

Cottage in Black Rock

Spacious Cottage Loft

Welcome to the Spacious Cottage Loft! Please enjoy a nice quiet relaxed atmosphere in this unique space. Its a little bit rustic with its shiplap pine and exposed beams. Its a little bit rock and roll with its little music space along with some favorite framed albums hanging on the walls. Very comfy queen size bed. 2 smart TVs (65" up & 55" down) for your entertainment pleasure. Roomy kitchen with brand new appliances. Bath-walk in shower. THIS SPACE IS DESIGNED TO ACCOMMODATE 1-2 GUESTS.

KitchenIndoor spacesHeating

4.95 out of 5 average rating, 108 reviews

The studio features a neatly arranged sleeping area with a quilted bedspread in blue and white patterns. A desk with a chair is positioned nearby, allowing for a focused workspace. Natural light streams through sheer curtains, creating a bright and welcoming ambiance.

Home in Bridgeport

Cozy Studio in Bridgeport

Charming and fully equipped studio located in the heart of Bridgeport. Perfect for business travelers, couples, or solo adventurers, this cozy retreat features a comfortable bed, high-speed Wi-Fi, a private entrance, and a fully stocked kitchen for your convenience. Enjoy easy access to local restaurants, cafes, and shops, as well as public transportation and major highways. Whether you’re here for work or leisure, this studio offers everything you need for a relaxing and stress-free stay.

Indoor spacesKitchenCleanliness

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.

4.99 out of 5 average rating, 184 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

KitchenFamilyNearby

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.

4.97 out of 5 average rating, 270 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!

Indoor spacesKitchenCheck-in

4.94 out of 5 average rating, 413 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

Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach

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.

FamilyKitchenLayout

4.93 out of 5 average rating, 288 reviews

Loft in Southport

Historic Loft, Co-Work, River View

Unique studio loft in a beautifully restored 19th-century Cider Mill on the Westport/Southport border. Enjoy picturesque river views, historic charm, and modern comfort. This pet-friendly retreat comfortably accommodates up to three guests, featuring a full kitchen, dedicated workspace, and access to a co-working space. Ideal for couples or solo travelers seeking a blend of history, convenience, and a serene setting with private parking.

FamilyIndoor spacesWifi

4.98 out of 5 average rating, 193 reviews

The bedroom features a queen size spindle bed with quality bedding, flanked by two nightstands with lamps. A dedicated work desk is equipped with a lamp and USB ports. Shelving adds storage, while a small seating area is present, illuminated by natural light from the windows.

Apartment in Fairfield

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

FamilyKitchenLocation

4.96 out of 5 average rating, 236 reviews

A private hot tub is situated beneath a covered patio, surrounded by blooming azaleas. The inclined garden path leads to a charming wooden house featuring a slate roof, with warm sunlight illuminating the scene. Outdoor seating is available nearby.

Home in Stratford

Cozy Colonial - Private Hot Tub & Entire House

The way Airbnb was meant to be, something special... a home away from home. No long rule book, just be respectful. Come and stay in this cozy colonial home centrally located in Stratford CT. Walk to the park, soak in the spa, sip tea, listen to music, play games, and relax. Less than 10 minutes from some of the best CT has to offer - beaches, shopping, restaurants, grocery, entertainment, hiking, train to NYC / Yale, and more.

Indoor spacesFamilyCheckout

4.88 out of 5 average rating, 161 reviews

A corner of the apartment features unique hand-tinted windows that create colorful reflections. A cozy armchair sits beside a fireplace, surrounded by potted plants. The space is complemented by a woven area rug and a light-colored bed with a simple texture.

Apartment in Bridgeport

Stylish Sheek Loft Ricport Studio 2, Downtown

Please note location and area before booking!!! (DONT BOOK if you don’t know it’s loud and busy) Conveniently located Downtown in the city of Bridgeport. Feel free to light a fire🔥. Unique hand tinted windows provides the space with an open feel although it is a small space. Queen size bed, fireplace, and aesthetics sets this apartment apart from any rental you can find. *pet fee for pets. Please let me know in advance.

KitchenIndoor spacesQuiet

4.96 out of 5 average rating, 226 reviews

Home in Fairfield

Cozy Cottage with Fire Pit, near Beach

Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities.

Indoor spacesKitchenTV

Guest suite in West Haven

The exterior of the midcentury home is presented among lush greenery, featuring a brown wooden facade and small windows. Vibrant flowering plants in shades of pink and green surround the area, providing a natural frame against the serene backdrop of trees and the nearby lake.

4.93 out of 5 average rating, 246 reviews

Midcentury Lakeside Guest Suite

Private guest studio suite in a beautiful, midcentury lakeside home. Built in 1957, this home on a quiet residential street is a unique piece of modern architecture around a serene lake in suburban Connecticut. It is walkable from the nearby railway station, and it is close to West Haven's picturesque beaches, and a short drive from downtown New Haven.

Indoor spacesKitchenCleanliness

Popular amenities for Bridgeport family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 145 reviews

Oceanfront Beach House w/ Private Hot Tub

FamilyKitchenAir conditioning

A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.

4.97 out of 5 average rating, 155 reviews

3 Bedroom Beach House with Hot Tub!

KitchenFamilyAccuracy

4.96 out of 5 average rating, 402 reviews

Cabin in New Fairfield

Little Lake Cabin— Lake Access, Hot Tub & Kayaks

KitchenIndoor spacesParking

4.96 out of 5 average rating, 207 reviews

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

Luxury cottage by the sea with hot tub and pool

Indoor spacesFamilyAir conditioning

4.96 out of 5 average rating, 142 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

FamilyKitchenParks

4.87 out of 5 average rating, 127 reviews

A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.

Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

FamilyKitchenBathroom

4.92 out of 5 average rating, 117 reviews

Home in Bedford

Bedford Paradise Getaway | Hot Tub | Town Center

FamilyKitchenAir conditioning

4.99 out of 5 average rating, 179 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 New Haven

A Spacious 5BR Near Yale|Ideal For Groups&Family

KitchenFamilyDecor

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 354 reviews

A rustic barn-style home features a wooden exterior with multiple large windows, enhancing natural light. A spacious elevated deck is surrounded by lush greenery, while an outdoor umbrella offers shade. The setting is serene, with a glimpse of the nearby brook and wooded area.

Home in Fairfield

Beautifully Restored Barn With New England Charm

KitchenIndoor spacesBathroom

4.94 out of 5 average rating, 102 reviews

A spacious living room features a large sectional sofa adorned with decorative pillows. A glass coffee table sits on a geometric patterned area rug. Natural light filters through sheer curtains, complemented by a modern light fixture and a wall-mounted television.

Apartment in Bridgeport

Polita’s Place #2

Indoor spacesFamilyHospitality

4.83 out of 5 average rating, 116 reviews

A cozy space is highlighted by natural light streaming through multiple windows. Two dogs sit on the hardwood floor between a staircase and a plush area. A potted plant adds a touch of green, while various furnishings are positioned throughout the room.

Home in Shelton

Mid-Century Modern House - Ciela Haus

KitchenFamilyLocation

5.0 out of 5 average rating, 124 reviews

A spacious living room features a large sectional couch adorned with colorful pillows, next to a smaller armchair. Natural light floods through wide windows framed by vibrant curtains. A wooden coffee table sits in the center, with art pieces displayed on the walls and a guitar nearby.

Home in New Haven

Westville Schoolhouse by Stephanie and Damian

KitchenFamilyHospitality

4.98 out of 5 average rating, 155 reviews

Fully renovated/Walk to water & shops/fenced yard!

KitchenIndoor spacesSleep quality

4.96 out of 5 average rating, 172 reviews

A dining table is set with two glasses of white wine beside a bottle. A vase with pink tulips is centered, while potted succulents are placed at either end. Soft natural light illuminates the table, creating a calm and inviting atmosphere.

Guesthouse in Fairfield

Cozy Home away from Home!

FamilyIndoor spacesCleanliness

4.84 out of 5 average rating, 172 reviews

The living room features a modern design with a curved green and orange sofa surrounding a light wood coffee table. A striking black fireplace provides a focal point against a light wall. A statue and decorative elements contribute to the welcoming ambience.

Home in West Haven

Westshore Luxury

FamilyKitchenBeach

4.84 out of 5 average rating, 122 reviews

A light-filled living area features a white sectional sofa and natural decor. Shelves with decorative items and plants enhance the space. The open layout leads to a dining area visible in the background, with wooden furniture and a textured rug grounding the room.

Home in Bethel

Boho house near NYC

Indoor spacesFamilyValue

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 159 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

Indoor spacesFamilyBeach

4.98 out of 5 average rating, 265 reviews

An aerial view showcases the antique farm property set within a spacious landscape. Surrounding areas feature a mix of treed land and open fields. The main house, along with additional structures and a large yard, is visible alongside winding roads, emphasizing the rural setting.

Barn in Bethel

Escape to a Restored New England Antique Milk Barn

KitchenFamilyBathroom

4.95 out of 5 average rating, 138 reviews

The living area features a light-colored sofa and accent chair positioned around a glass coffee table. Large windows allow natural light to enter, while sheer curtains frame the view of the outdoor space. A television and elegant decor add comfort to the setting.

Apartment in New Haven

King 1BR Apt with Cozy Den and Luxury Amenities

FamilyKitchenBathroom

5.0 out of 5 average rating, 187 reviews

A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

Indoor spacesKitchenView

4.97 out of 5 average rating, 213 reviews

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

Garden Level Suite with Beautiful Pool

Indoor spacesFamilyLocation

4.92 out of 5 average rating, 233 reviews

A charming guest studio is set among trees, featuring large glass doors that open to a stone patio. Four white adirondack chairs surround a fire pit, providing a relaxed outdoor gathering space. The studio's design reflects a serene and inviting atmosphere in nature.

Guesthouse in Bedford

Private Guest Studio

FamilyKitchenValue

4.96 out of 5 average rating, 269 reviews

A spacious outdoor pool is surrounded by natural greenery, featuring a stone patio and a diving board. A covered lounge area with large windows overlooks the pool, providing a serene setting for relaxation and leisure.

Home in Stamford

Midcentury Modern ZenHouse Sculptor Studio

FamilyKitchenComfort