Family-friendly vacation rentals in Port Chester

4.91 out of 5 average rating, 144 reviews

A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.

Home in Rye

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

KitchenFamilyCheckout

4.8 out of 5 average rating, 127 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 Port Chester

Greenwich abode Close to Just about Everything

2 - Bedroom apartment in a duplex. 4 - Minutes to Greenwich Avenue Shopping 6 - Minutes to Port Chester restaurants 8 - Minutes to Rye town and restaurants. 5 - Minutes to The Capital Theater 5 - Minutes to Byram Beach 10- Minutes to Tod's Point Beach 4 - Minutes by car to Greenwich and Port Chester Metro North Station 1 - Twin Air Mattress, SERTA auto inflate, 15inch raised {UPON REQUEST } Private and cozy retreat, steps away from one of Greenwich's Top Beaches - Byram Shore Beach Club.

KitchenFamilyAccess

4.91 out of 5 average rating, 176 reviews

A spacious living room featuring a comfortable sectional sofa adorned with decorative pillows. A large area rug anchors the seating arrangement, which includes two lounge chairs. Natural light filters through multiple windows, highlighting the neutral color palette and decorative wall art.

Home in White Plains

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

KitchenFamilyTV

A well-lit living room features a light-colored sofa adorned with cushions, paired with a wooden coffee table. A television is mounted on the wall, while a glass-fronted cabinet displays decorative items. Light streams through large windows, highlighting the warm wooden floor.

4.83 out of 5 average rating, 218 reviews

Gem by the water+ firepit and all fenced backyard

An episode of The Curious Case of… was filmed right here at the property. Stay where the cameras rolled and experience the same atmosphere that caught the producers’ attention. One block away from the water & 3 blocks away from Dolphin Cove. Enjoy walking and site-seeing. 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. The house has also a lower-level unit.

FamilyIndoor spacesComfort

4.76 out of 5 average rating, 410 reviews

Apartment in Greenwich

Flex Comfort Apts of Greenwich #2

Flex Comfort Apt #2 is 2 Bedroom / 1 Bath and sleeps 4. Apt #2 is the middle floor of a 3 apartment building. Private Parking & Entrance. Great mattresses, linens, big screen smart TVs, multiple desks, and clean. Well stocked kitchen to put on a family meal. Get the value of 2 x hotel rooms for the price of one that includes your own kitchen and Family Room. 1 Mile from Greenwich Train station - 45 mins to Grand Central. Easy access to 95 and everything CT & NY have to offer.

Indoor spacesFamilyBeach

Townhouse in White Plains

A dining area features a large rectangular table surrounded by six sleek black chairs. Above, a modern light fixture with five shades illuminates the space. Artwork is displayed on the walls, and a green plant adds a touch of nature, enhancing the inviting atmosphere.

Stylish 4bed 2bath Home in White Plains

Our renovated townhouse, a perfect blend of suburban calm & NYC charm, is your home away from home. This stylish & peaceful accommodation, situated right outside White Plains downtown, affords you effortless access to train stations, freeways, and vibrant restaurants & shops. With a well equipped kitchen, 2 full baths, and 4 bedrooms spreading across 3 floors, it has everything you need whether you come to visit family, for business, or to simply seek an escape from the bustling big city life.

KitchenIndoor spacesLong stay

4.94 out of 5 average rating, 125 reviews

4.89 out of 5 average rating, 123 reviews

Home in Mamaroneck

Entire 2nd floor House: yard, parking, train NYC.

Entire 2nd floor of our house with private entrance. Enjoy this cozy and very newly renovated 2 + bedroom, couch'TV, WIFI, free street or back yard parking. The train is literally 2 blocks away ,Metro North, quick way to NYC to avoid parking. A few blocks from downtown Mamaroneck with dozen of restaurants and the harbor/beach under a 10 minute walk. With a washer & Dryer, Full kitchen, table and chairs, folding couch and love seat. You'll have a great time at this comfortable place to stay.

FamilyIndoor spacesValue

4.97 out of 5 average rating, 119 reviews

A cozy living room features a large flat-screen TV mounted on the wall, accompanied by a sleek entertainment unit. A comfortable couch is draped with a soft blanket, and an armchair is positioned nearby. Natural light enters through two windows, brightening the neutral decor.

Guesthouse in Mamaroneck

Spacious guest suite near water

Welcome to your perfect home away from home! Enjoy a spacious and newly renovated basement suite with windows and separate entrance in a private house, perfect for up to four guests. Ideal for couples, small families, or business travelers. This cozy retreat, combines privacy and comfort in a quiet neighborhood. Whether you’re here for a short trip or an extended stay, this apartment offers everything you need for a comfortable and relaxing experience. Book now and start planning your visit.

FamilyKitchenValue

4.99 out of 5 average rating, 113 reviews

A modern kitchen is equipped with stainless steel appliances and granite countertops. Upper cabinets with illuminated displays complement the warm-toned backsplash. A vase filled with fresh flowers enhances the countertop space, while the polished wood flooring stretches across the area.

Home in Mamaroneck

Entire 4BR House, Walk to Train! Yard + Parking

Enjoy the 4BR/2BA house to yourself in one of Westchester’s most family-friendly communities, <40 min from NYC. Ideal for families (dog friendly, 1 per stay), relocations and longer stays, with a fenced yard, parking, fast Wi-Fi, washer/dryer and kid essentials (a crib, bassinet & more). Walk to Metro-North (13 min), stores, restaurants and Mamaroneck Ave. Kids will love the fenced yard and Florence Park down the block, with a playground, basketball and tennis. Need a longer stay? Ask us!

Indoor spacesKitchenParks

4.94 out of 5 average rating, 108 reviews

5BR Beach House, Game Room + Huge Backyard

Escape to this spacious 5-bedroom Shippan beach home, designed for families and groups to relax, reconnect and have fun together. Just a short walk from West Beach, the home features a huge private fenced backyard, two large decks, fire pit, game room, pool table, ping pong, foosball and plenty of indoor and outdoor space for everyone to spread out Located just minutes from Downtown Stamford and Metro-North, it’s an ideal home base for family getaways, group stays and corporate retreats

KitchenFamilyPool

A sunroom features light blue walls complemented by natural light from the large windows. Two rocking chairs are positioned beside a wooden table. Decorative mirrors reflect the cozy ambiance, while soft curtains frame the windows, providing a serene and inviting space.

4.97 out of 5 average rating, 115 reviews

Seashell Bungalow | 3 Bed 1 Bath | Beach House

Seashell Bungalow - located in Stamford, just a stone's throw from NYC. Less than a 2-minute walk from the beach. Perfect for those looking to enjoy the tranquility of the beach with the city life nearby. Outdoor dining area - perfect for summer evening relaxation. Fully equipped for fun and adventure - paddle boards and various games available. Ideal for family vacations or a friends’ getaway. Book your stay today and enjoy an unforgettable beachside adventure!

Indoor spacesFamilyLaundry

Apartment in Port Chester

A cozy living room features a large sectional sofa adorned with decorative pillows. A glass coffee table sits on a soft area rug, while a flat-screen TV is mounted on the wall. Two windows allow natural light to fill the space, enhancing its inviting atmosphere.

Sunny & Cozy Stay by Capitol Theatre/Downtown

Within walking distance of downtown Port Chester, Capitol Theatre, Metro North, and so much more; this 2 bedroom apartment with PRIVATE ENTRANCE provides a comfortable, inviting stay for those visiting the New York City/Metropolitan area. We are centrally located near the I-287, I-95, so commuting to and from the area is easy.

KitchenIndoor spacesAir conditioning

4.98 out of 5 average rating, 131 reviews

Popular amenities for Port Chester family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 145 reviews

A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.

Barn in Katonah

Magic Red Barn with Heated Salt Pool (opened now)

FamilyIndoor spacesPool

4.99 out of 5 average rating, 186 reviews

Home in Commack

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

FamilyIndoor spacesWalkability

4.91 out of 5 average rating, 156 reviews

The home theater features a large screen and 15 electric recliner seats arranged in a semi-circle. Dark blue walls and patterned carpeting create a cozy movie-watching environment. Subtle lighting enhances the overall ambiance without overwhelming brightness.

Guest suite in Northport

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

KitchenFamilyBackyard

4.92 out of 5 average rating, 119 reviews

Home in Bedford

Bedford Paradise Getaway | Hot Tub | Town Center

Indoor spacesKitchenAccess

4.95 out of 5 average rating, 111 reviews

The exterior of the home is portrayed at dusk, surrounded by trees. A spacious deck with outdoor seating is visible, along with an oversized hot tub lit by soft lights. Large windows reveal an inviting interior, contributing to the serene ambiance.

Villa in Tuxedo Park

Tuxedo Hilltop Retreat with a Large Hot Tub

KitchenFamilyView

Sailboats glide across a calm blue sea, with distant shorelines visible under a clear sky. The tranquil waters reflect shades of blue, creating a serene nautical setting that accentuates the beauty of the surrounding landscape.

4.94 out of 5 average rating, 120 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

KitchenFamilyBreakfast

4.96 out of 5 average rating, 139 reviews

A relaxing hot tub is illuminated with soft blue lighting, featuring a pink flamingo float. String lights provide a gentle glow overhead, enhancing the serene evening ambiance. The surrounding area is enclosed for privacy, offering a tranquil retreat.

Home in Elmont

MOON & SPA near JFK | UBS

KitchenIndoor spacesLayout

4.96 out of 5 average rating, 212 reviews

A private hot tub with soft blue lighting is surrounded by an inviting backyard space. String lights create a warm ambiance overhead, enhancing the outdoor seating area with comfortable furnishings. A staircase leads to the entrance of the home, partly visible in the background.

Guest suite in Elmont

Private Studio & SPA near JFK| UBS arena.

Indoor spacesFamilyLocation

Family- and pet-friendly home rentals

Apartment in New Rochelle

A spacious bedroom is presented, featuring a sizable bed dressed in soft white linens and accented by numerous decorative pillows. Two lamps provide gentle illumination on either side, while artwork adorns the walls. A wooden bench is positioned at the foot of the bed.

Woven Winds Retreat

Indoor spacesKitchenBackyard

4.99 out of 5 average rating, 199 reviews

A charming country house with a mix of siding colors, framed by lush greenery and landscaped gardens. The structure features multiple gables, large windows, and a two-car garage with a gravel driveway leading to the entrance.

4.98 out of 5 average rating, 260 reviews

Bright Stylish Chic 4BR 4BA Home

FamilyKitchenBackyard

4.98 out of 5 average rating, 152 reviews

A charming two-story house is presented, featuring a stone facade and white trim. Lush greenery surrounds the home, with a large tree providing shade in the front yard. A wide staircase leads to the welcoming front porch, enhancing the inviting appearance of the entrance.

Home in Mamaroneck

Bright & Modern Victorian in NY Suburbs

FamilyKitchenView

4.86 out of 5 average rating, 233 reviews

A cozy living room space is furnished with a dark sofa and a coffee table featuring a decorative arrangement. Shelving units display various decorative items, while natural light comes through a window dressed with sheer curtains.

Apartment in Stamford

HighLineHarbor Flat2BD|Train2NYC|HarborPointAccess

FamilyIndoor spacesCheck-in

4.92 out of 5 average rating, 138 reviews

A spacious living area is seen, featuring a blend of comfortable seating options, including two sofas and several armchairs. A coffee table sits on a large area rug, and a dining table is positioned nearby. Natural light floods the room through multiple windows, enhancing the bright atmosphere.

Townhouse in Greenwich

Walk to Greenwich Ave [KING bed] BEST Location

KitchenFamilyGetting around

4.94 out of 5 average rating, 101 reviews

Apartment in Stamford

Seabreeze at the beach, west beach stamford, Ct

Indoor spacesKitchenParking

4.98 out of 5 average rating, 142 reviews

A bright living area is present, featuring a comfortable white sofa with blue accent pillows and a natural woven rug. A modern coffee table is placed in front, while large windows allow ample natural light. A fireplace adds a cozy focal point, complemented by a TV mounted above.

Home in Norwalk

Family Cottage with 4 King Beds and Fire Pit

Indoor spacesKitchenParking

4.99 out of 5 average rating, 170 reviews

Guesthouse in Rowayton

1BR full cottage, 1 min walk to private beach

Indoor spacesFamilyValue

Family-friendly home rentals with a pool

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 spacesKitchenTV

4.98 out of 5 average rating, 102 reviews

A warm wooden interior is featured, with wall art depicting horses and rural scenes. A rustic wooden table is positioned near the window, and a candle sits at its center. A potted plant adds a touch of greenery beside a cozy armchair.

Farm stay in Redding

Charming Historic Cottage in the Redwoods

KitchenIndoor spacesWifi

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

KitchenFamilyHeating

4.95 out of 5 average rating, 135 reviews

An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.

Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

KitchenFamilyLocation

4.88 out of 5 average rating, 228 reviews

A spacious living area exhibits warm wooden floors and large windows adorned with decorative curtains. A cozy futon is positioned on a textured rug, complemented by a decorative welcome sign on the wall. A spiral staircase leads to the upper level, enhancing the open layout.

Apartment in Stony Point

E and T Getaway LLC

FamilyKitchenGetting around

4.91 out of 5 average rating, 143 reviews

A spacious backyard features a rectangular pool surrounded by a wooden deck. Several lounge chairs are positioned along the deck, complemented by an umbrella for shade. Lush greenery lines the perimeter, creating a serene outdoor atmosphere.

Home in Massapequa

Great Family Times in this 5 Bedroom House

FamilyKitchenLong stay

Guest suite in Massapequa

A well-lit studio space features a Murphy bed with soft bedding, ready for use. A flat-screen TV is mounted on the wall opposite. A black dresser with woven baskets provides storage, complementing the simple, clean design of the room.

Private Murphy Bed Style Studio

KitchenFamilyAccuracy

4.87 out of 5 average rating, 119 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.