Family-friendly vacation rentals in Woodbridge

4.75 out of 5 average rating, 565 reviews

An open bedroom suite is featured, with a warm-colored comforter covering a spacious bed. A wooden dresser stands beside the bed, and a leather couch is positioned against the wall. Natural light enters through windows, brightening the neutral-toned walls.

Guest suite in Ansonia

Private Inn

Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

FamilyIndoor spacesWalkability

A bright living space is depicted with light wooden flooring. A cozy seating area features a blue sofa facing a simple white table. Behind the table, a wooden dining set with four chairs is visible. Shelves with decor adorn the walls, and a kitchen area can be seen in the background.

4.94 out of 5 average rating, 175 reviews

Downtown Elegant Stay By Yale • Rooftop • Gym

Come and stay at this luxury, modern one-bedroom apartment just steps away from Yale! With Broadway just around the corner and some of New Haven’s best Pizza a stone’s throw away you’d be hard-pressed to find a better location for your stay. Enjoy cooking up a nice dinner at home one night using the fully-equipped kitchen provided. Spend the evening on the rooftop terrace watching the sunset over the city skyline before tucking in for the night. Use the downstairs gym for a morning workout.

FamilyKitchenCheck-in

A cozy living space features a light-colored sofa with yellow accents, positioned beside a small round table. A striped area rug adds texture to the hardwood floor. Bright natural light enters through nearby windows, illuminating the space and connecting to the kitchen and bathroom beyond.

4.98 out of 5 average rating, 305 reviews

Bright 1 BR Apt Steps From Yale

Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

KitchenIndoor spacesValue

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.

4.96 out of 5 average rating, 137 reviews

King 1BR Apt with Cozy Den and Luxury Amenities

This gorgeous apt, located in a brand-new luxury building at the center of New Haven’s historic downtown, offers unparalleled comfort, service, and amenities. You can watch a movie on a 65" HDTV, work in one of 5 co-working spaces, or relax at the pool w/ grills and cabanas. Highlights: • Walkable access to Yale • Deep-clean prior to every guest • Coffee, fresh linens, and bathroom essentials • 24/7 fitness center • Rooftop sun terrace + grills • Entertainment lounge w/ bowling alley

Indoor spacesKitchenCleanliness

A cozy living room features a spacious blue couch adorned with yellow accent pillows. A wooden coffee table is positioned in front, with colorful artwork hanging on the walls. A large flatscreen TV is mounted for entertainment, enhancing the comfort of the space.

4.94 out of 5 average rating, 157 reviews

Retreat in New Haven by Stephanie and Damian

Welcome to your retreat in the heart of Westville. This apartment features a spa-like bathroom and a cozy living room with a super-comfy couch and large flatscreen TV. Relax in this centrally located oasis near Yale’s football stadium, Westville Bowl, local art studios, coffee shops, and top restaurants just steps away. Perfect for extended stays, traveling professionals, visiting faculty, or anyone seeking a convenient home base this winter. Discounts for stays of 30+ days.

Indoor spacesFamilyCondition

4.96 out of 5 average rating, 137 reviews

A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.

Cottage in Seymour

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

KitchenIndoor spacesCheckout

4.89 out of 5 average rating, 244 reviews

An elegant entryway frames a view of a dining area furnished with a large wooden table surrounded by chairs. A vintage-style bar cart, stocked with various beverages, is positioned to one side, contributing to a refined atmosphere. Warm wood accents complement the bright and inviting space.

Home in New Haven

Large Designer Westville house! Walk to Yale Bowl

Large pristine 2 bedroom, perfect location, set up specifically for the luxury traveler. Central a/c and heat. Cozy living room with extra large, sofa, well-stocked kitchen, huge dining table, comfortable and very quiet bedrooms with black out curtains, memory foam mattresses (Tuft & Needle), and super soft sheets bamboo cooling sheets. Centrally located house with all the amenities of home. Safe and quiet, cute walk-able area!

FamilyKitchenParks

A cozy sleeping area features a wooden bed frame adorned with decorative pillows, flanked by two bedside tables. A light blue throw is draped over the bed. A comfortable seating area includes a round table and armchair, complemented by a soft rug covering the floor.

4.93 out of 5 average rating, 352 reviews

Modern Urban Getaway | Near Yale + Downtown

Beautiful and private Airbnb apartment located in New Haven. Peaceful, bright, immaculate and thoughtfully appointed is the best way to describe the Urban Sanctuary. You will fall in love with our cozy and charming garden apartment, nestled in a historic 3 family home in Westville. You will find good restaurants and coffee shops around, it's just the best place for you to stay. We provide a variety of amenities.

Indoor spacesKitchenSleep quality

A well-lit kitchen area features a white refrigerator and a gas stove, complemented by a central island with a grey countertop. A plant is situated on the windowsill, while a vase of flowers adds a touch of color to the space. A decorative rug enhances the cozy ambiance.

4.78 out of 5 average rating, 387 reviews

Cozy 2 Bedroom rental on Elm…

This special place is close to everything, making it easy to plan your visit. It’s in the city and close to just about all of your wants and needs. Lots if fine dining, Universities and fun shops that are a must see. Also conveniently located so you don’t need a car to get around. I’m also very glad to help with any questions, or if you just need suggestions on places to go or things to do. Hope to see you soon.

FamilyKitchenCheck-in

Guest suite in Woodbridge

A spacious two-story house is framed by lush green grass and landscaped gardens. A circular driveway leads to the entrance, flanked by trimmed hedges and a small tree at the center of a mulched bed. Large windows reflect the surrounding greenery.

4.92 out of 5 average rating, 170 reviews

Cupola Hill -a 2 BR guest suite with bucolic views

Beautiful 2 bedroom guest suite attached to main house with separate entrance, bathroom, living room. Set on magnificent 20 acre estate, perfect country get away, only 15 minutes to Yale and downtown New Haven. It’s the best of both worlds! Come enjoy the great restaurants of New Haven and then head to Cupola Hill for an evening in the country! Have a glass of wine under the stars and watch the wildlife!

Indoor spacesFamilyQuiet

4.97 out of 5 average rating, 111 reviews

Soaking Tub Retreat | Cozy Luxe Stay Near Yale

Relax in this peaceful retreat just 10 minutes from downtown New Haven and Yale. Ideal for solo travelers or anyone seeking a quiet escape. Enjoy the deep soaking tub, calming decor, fast Wi-Fi, and a serene space to recharge. No parties—just peace, comfort, and good vibes. This is a calm, intentional space for peaceful stays only. We welcome guests who appreciate good energy and quiet rest.

KitchenFamilyQuiet

4.95 out of 5 average rating, 128 reviews

A spacious living area features large windows allowing natural light to fill the room. A sectional sofa and armchair are arranged around a decorative rug. A television is positioned on a wooden cabinet, and a plant adds a touch of greenery to the decor.

Apartment in East Rock

Apartment in New Haven

This is a luxurious and spacious apartment on the ground floor of a historic home, centrally located in the heart of East Rock. It is a 5 min drive (or 20 min walk) from Yale's campus and there is a shuttle stop right next to the house on Whitney (blue/orange lines). The master bedroom has a king bed and a private shower/bathroom. The guest bedroom has a queen bed and library.

Indoor spacesFamilyLaundry

Popular amenities for Woodbridge family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 125 reviews

A tranquil enclosed sunroom features two white cushioned chairs and a wooden table, all overlooking the serene lake. Large windows provide expansive views of the water and surrounding greenery, creating a peaceful atmosphere for relaxation.

Bungalow in Plymouth

Lakefront Bungalow Bliss | Serene 2BR Retreat

KitchenFamilyValue

4.96 out of 5 average rating, 206 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 spacesKitchenHospitality

4.88 out of 5 average rating, 74 reviews

An outdoor space features a heated pool with a clear blue surface, surrounded by a spacious deck. Lounge chairs and shaded seating areas are arranged nearby, offering comfort and relaxation. Lush greenery borders the area, enhancing the tranquil atmosphere.

Home in Hamden

Modern home with a private Heated pool and jacuzzi

KitchenFamilyPool

4.94 out of 5 average rating, 145 reviews

Home in Milford

Oceanfront Beach House w/ Private Hot Tub

KitchenIndoor spacesAir conditioning

4.87 out of 5 average rating, 171 reviews

A comfortable living space is presented, combining a light-colored sofa and a larger grey sectional couch. A wooden coffee table sits centrally, with artwork displayed on the wall above. Soft lighting is provided by overhead fans, enhancing the cozy atmosphere.

Guest suite in Waterbury

Private cozy getaway

KitchenFamilyLayout

4.99 out of 5 average rating, 167 reviews

The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.

Cottage in Bethlehem

Cozy Cottage |Quintessential CT | Pet Friendly

Indoor spacesFamilyWifi

4.96 out of 5 average rating, 141 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

Indoor spacesKitchenTV

5 out of 5 average rating, 69 reviews

Home in Guilford

Field of Dreams Hot Tub - Fire Pit Retreat

FamilyIndoor spacesLayout

Family- and pet-friendly home rentals

4.78 out of 5 average rating, 124 reviews

Apartment in Wallingford

Wallingford Getaway

Indoor spacesFamilyAmenities

4.84 out of 5 average rating, 168 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

Indoor spacesFamilyTV

4.96 out of 5 average rating, 345 reviews

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.

Apartment in Southport

2BR Flat above Historic Cider Mill

Indoor spacesKitchenCheckout

4.82 out of 5 average rating, 260 reviews

A rustic cabin with green log siding is surrounded by tall trees. The front porch features two black chairs, and a storage trunk adds a practical touch. A decorative star and wall clock enhance the inviting exterior, while a garden area complements the natural setting.

Bungalow in Trumbull

Cozy, romantic cabin by the lake.

FamilyKitchenCleanliness

4.94 out of 5 average rating, 410 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

FamilyKitchenPets

4.93 out of 5 average rating, 294 reviews

A well-maintained front yard is seen, featuring a manicured lawn and flower beds. Brick planters with blooming flowers add color. The residence showcases a brick facade with a chimney and is surrounded by greenery, providing a serene and inviting appearance.

Apartment in Waterbury

Private 1 bedroom apartment in central Connecticut

FamilyKitchenQuiet

4.95 out of 5 average rating, 104 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

KitchenIndoor spacesHeating

4.98 out of 5 average rating, 170 reviews

A timber-style cottage is surrounded by landscaping featuring stones and low shrubs. A spacious deck with white railings leads to a welcoming entrance. Light-colored siding and multiple windows enhance the two-story structure, set against a backdrop of trees and open land.

Home in Southbury

The Cottage at Cedar Spring Farm

KitchenFamilySleep quality

Family-friendly home rentals with a pool

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

Indoor spacesFamilyAccuracy

4.8 out of 5 average rating, 15 reviews

The entryway is illuminated by three pendant lights, leading to an expansive outdoor view through double doors. A patterned tile floor contrasts with wood trim and walls, while potted plants and flowers add a touch of nature to the welcoming space.

Home in Oxford

Gorgeous Luxury INDOOR POOL home

Indoor spacesKitchenLocation

4.97 out of 5 average rating, 212 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

FamilyKitchenLong stay

4.93 out of 5 average rating, 82 reviews

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

Cozy studio unit

KitchenIndoor spacesLong stay

4.98 out of 5 average rating, 111 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

KitchenIndoor spacesCondition

4.86 out of 5 average rating, 21 reviews

Home in Redding

Meeker Hill House - Country Escape with Heated Poo

Indoor spacesKitchenCondition

4.98 out of 5 average rating, 158 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

FamilyKitchenCleanliness