Family-friendly holiday rentals in New Haven

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, 310 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.

A rooftop terrace is shown, featuring a round table and two high black chairs. The space offers an unobstructed view of the city skyline, showcasing various buildings under a clear blue sky with scattered clouds.

4.94 out of 5 average rating, 180 reviews

Elegant Modern Stay Near Yale • Gym • Roof Terrace

Come and stay at this luxury, modern one-bedroom apartment just steps away from Yale! Broadway lies 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.

A serene view of the Long Island Sound showcases several sailboats gently drifting on the blue water. The scene is framed by a simple fence and grassy area, with a clear blue sky above, creating a peaceful coastal atmosphere.

4.98 out of 5 average rating, 231 reviews

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

PETS ALLOWED! Spectacular unobstructed Long Island Sound views year-round, out your front door along Pardee Seawall! This exceptional shore line property offers all new furniture & amenities. Minutes to wedding venues-perfect for getting dressed on your wedding day & taking photos literally right outside your door (props available). Near: Tweed NH Airport, beach, Yale University & Hosp, restaurants & museums. All new furniture, linens/towels, grill, fire pit, centralAC, WIFI. Onsite parking.

4.88 out of 5 average rating, 109 reviews

A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.

Cottage in Milford

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

4.99 out of 5 average rating, 109 reviews

Home in Branford

Steps to Beach • Hot Tub • Game Room • Water Views

Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.

A bright living area features large windows, allowing natural light to fill the space. A comfortable gray sofa sits alongside a round coffee table and a cozy armchair. The open kitchen is equipped with modern appliances and sleek cabinetry, ideal for a relaxing stay.

4.95 out of 5 average rating, 125 reviews

Luxurious 3BR Apartment w/ Parking & Gym

Our prime location meets modern elegance. This three-bedroom spacious apartment is designed for comfort, convenience, and sophistication in the heart of a dynamic urban community. Whether planning a quiet night in or a lively evening downtown, Hyatus amenities elevate your living experience. º Rooftop Sky Lounge with an outdoor TV º Screening area º Cabanas º Billiards º Bocce courts º Fireside lounge º Co-working space featuring private work pods º Meeting rooms º Cappuccino Bar

A bright and modern kitchen area features white cabinetry and stainless steel appliances. A large island is equipped with seating for three, while a cozy living space with two leather chairs is visible in the background. Natural light filters through multiple windows.

5.0 out of 5 average rating, 204 reviews

The Winchester House at Science Park-Yale

Located 2 blocks from Yale University's Franklin and Murray College and Ingall's Ice rink, The Winchester House at Science Park is a newly renovated luxuriously appointed 2 bedroom 2.5 bathroom apartment. The apartment features bespoke amenities, free secure off-street parking, snacks and beverages, stylish furniture, 1000 ct. beddings, ample cooking pantry items and everything you need as a guest. Let us welcome you in relaxed luxury!

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, 394 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.

4.97 out of 5 average rating, 115 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.

4.93 out of 5 average rating, 136 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.

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.

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.

4.93 out of 5 average rating, 254 reviews

4.99 out of 5 average rating, 177 reviews

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

Ecape to the charming beach community of Indian Cove in Guilford and unwind in this beautifully renovated 1920s coastal cottage. Full of character and warmth, this spacious retreat blends historic charm with modern comfort-featuring wood floors, high beam ceilings, and a stunning stone fireplace that creates the perfect cozy atmosphere year round.

Popular amenities for New Haven family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 210 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

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.

4.96 out of 5 average rating, 146 reviews

Beach Haven - waterfront, near Yale, sunsets

4.96 out of 5 average rating, 239 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

4.97 out of 5 average rating, 156 reviews

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.

Home in Milford

3 Bedroom Beach House with Hot Tub!

4.88 out of 5 average rating, 129 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

4.88 out of 5 average rating, 176 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

4.91 out of 5 average rating, 74 reviews

New Haven Home | Private| Groups| Yale | Hot Tub

4.81 out of 5 average rating, 230 reviews

Home in West Haven

Beautiful Bayfront Home • Heated Pool & Jacuzzi

Family- and pet-friendly home rentals

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.

5.0 out of 5 average rating, 127 reviews

Westville Schoolhouse by Stephanie and Damian

4.94 out of 5 average rating, 307 reviews

The sunroom features a light pink wall and a high ceiling with exposed beams. A comfortable wicker sofa with decorative throw pillows accompanies two matching chairs. A patterned area rug covers the floor, while a small table sits in the center. Soft light filters through sheer curtains.

Cottage in Guilford

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

4.95 out of 5 average rating, 215 reviews

A living room area features a comfortable blue sofa adorned with decorative pillows. Two side tables with lamps provide light, while a round coffee table with a decorative centerpiece sits in the middle. A patterned area rug with ocean motifs enhances the atmosphere.

Guest suite in New Haven

Renovated Studio 1Bd/ 1BA/ kitchen All Private

4.85 out of 5 average rating, 268 reviews

Cottage in Branford

Cozy 2 Story Cottage in Short Beach Community

4.83 out of 5 average rating, 241 reviews

Apartment in East Rock

English Garden Studio, sleeps 3, Pet Friendly

4.98 out of 5 average rating, 114 reviews

The exterior of a private guest house is depicted, showcasing a blue facade complemented by multiple windows. A spacious stone patio features outdoor seating surrounded by lush greenery and garden flowers. The roof is sloped, and trees provide a natural canopy overhead.

Guesthouse in Guilford

Page Guest House

A large brick house with a distinctive gabled roof and charming architectural details is surrounded by lush greenery and blooming flowers. The welcoming exterior features well-maintained landscaping and pathways leading to the entrance. The sky is clear, contributing to a bright and airy appearance.

4.98 out of 5 average rating, 123 reviews

Large group haven! Sleeps up to 20!

4.88 out of 5 average rating, 109 reviews

A comfortable bedroom features a spacious bed with soft pillows and a decorative throw. Shelves adorned with framed botanical art and trailing greenery enhance the calming space. Natural light streams through semi-sheer curtains, complementing the neutral color palette.

Apartment in East Rock

King Bed/ 5 min to Yale/ East Rock Gem

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 162 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

4.97 out of 5 average rating, 214 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

4.98 out of 5 average rating, 113 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

4.94 out of 5 average rating, 63 reviews

Barn in Roxbury

Classic Red Barn with game room and gym

5.0 out of 5 average rating, 79 reviews

The outdoor pool area features a well-maintained rectangular pool, surrounded by a paved patio. Comfortable seating arrangements with red cushions are positioned nearby. Sunset colors illuminate the sky, and lush greenery and fields are visible in the background, creating a serene atmosphere.

Loft in Branford

Shoreline Carriage House

4.92 out of 5 average rating, 89 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

4.76 out of 5 average rating, 17 reviews

Home in Newtown

Colonial yellowhouse