Family-friendly holiday rentals in Mamaroneck

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!

FamilyKitchenPets

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!

Indoor spacesKitchenOutdoor spaces

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.

FamilyIndoor spacesOutdoor spaces

4.94 out of 5 average rating, 125 reviews

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 spacesFamilyAccess

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.

KitchenFamilyHospitality

4.95 out of 5 average rating, 153 reviews

A modern kitchen is highlighted by white cabinetry and a contrasting dark tile floor. Stainless steel appliances are positioned along the wall, while a spacious island offers additional counter space. A window allows natural light to fill the area, complementing the neutral color palette.

Home in Mamaroneck

Fully renovated 3 bedroom, 2 bath private home

Come and enjoy our beautifully renovated 3 bedroom, 2 bath home. A fully stocked kitchen with stainless steel appliances await. There is a king size bed (bedroom 1) and two twin beds (bedroom 2) and a twin size bed plus dedicated work space (bedroom 3). Plenty of storage space. Washer, dryer and second bathroom are downstairs. Private driveway. Fenced backyard space w/patio set. We are three blocks away from Metro North, and Mamaroneck Village, which has some the best restaurants around.

Indoor spacesKitchenGetting around

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.

FamilyIndoor spacesTV

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!

KitchenFamilyComfort

4.94 out of 5 average rating, 108 reviews

Home in Stamford

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

Indoor spacesFamilyCleanliness

4.96 out of 5 average rating, 330 reviews

A well-appointed kitchen features wooden cabinetry and modern appliances. A round dining table is set for two, complemented by a vibrant plant centerpiece. The space is illuminated with soft lighting, enhancing the inviting atmosphere while maintaining ample counter space.

Apartment in Harrison

Luxury Private Apartment - Walk to Train for NYC!

Luxury Large Private One Bedroom Apartment. With private walkway and entrance. Full Kitchen with New Appliances. King size Bed with Move Projector and Screen. Large couch with Desk in Living room. Updated Bathroom with Bathtub. Walking Distance to Harrison Train Station - Harrison Metro North Train Station access to New York City or Greenwich / Stamford CT. To Grand Central Station. Walking Access to local Parks.

KitchenFamilyLong stay

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

Looking to escape the city for some much-needed rest and relaxation? Come and enjoy our spacious apartment, featuring two bedrooms, one bathroom, a fully equipped kitchen, and a large living and dining area. Want to spend time outdoors? Step outside to our sizable backyard with an enclosed pavilion with lounging furniture. An added bonus: we're only 10 minutes away from Orchard Beach!

FamilyKitchenLocation

4.99 out of 5 average rating, 199 reviews

Apartment in New Rochelle

A cozy living area is highlighted by a mounted television above an elegant white mantle. A decorative rug with intricate patterns covers the floor, complementing the gray walls. Doorways lead to adjoining rooms, providing a sense of openness and accessibility.

New Rochelle Apartment

Enjoy a stylish experience at this centrally-located place. Located in Downtown New Rochelle. 5 min drive/12 min walk to train station. A 30-minute train ride away from Grand Central. Right next to 24-hour CVS, 24-hour McDonald's, Taco Bell, Starbucks & Sunoco (Gas station). Laundromat Becky's Bubbles is located two blocks away.

Indoor spacesFamilyCondition

4.86 out of 5 average rating, 151 reviews

Popular amenities for Mamaroneck family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 186 reviews

Home in Commack

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

FamilyIndoor spacesParks

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)

KitchenFamilyLocation

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

FamilyKitchenBackyard

4.97 out of 5 average rating, 108 reviews

A spacious two-story house features a covered porch with white railings, providing a welcoming outdoor area. Lush green grass surrounds the property, and the backdrop includes rolling hills and a clear sky with clouds, emphasizing the serene location near the water.

Villa in Greenwood Lake

Hillside villa with 9-mile lake views

FamilyIndoor spacesBathroom

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

FamilyKitchenDecor

4.9 out of 5 average rating, 277 reviews

A spacious bedroom features two queen-sized Memory Foam beds dressed in high-quality linens. A light blue and white striped wall design complements the neutral carpet. A stylish chair and a decorative lamp add to the inviting ambiance, while framed images enhance the aesthetic.

Guest suite in Baldwin

Vintage living.

FamilyKitchenParks

4.92 out of 5 average rating, 167 reviews

A spacious living room features royal blue couches surrounding a central coffee table. Natural light floods the area through large sliding doors and a skylight, highlighting a brick accent wall and a fireplace. A decorative plant adds a touch of greenery.

Home in Chester

Serene Private Home • Light-Filled • Hot Tub •Deck

KitchenFamilyCheckout

4.96 out of 5 average rating, 327 reviews

A six-person Jacuzzi hot tub is positioned on a patio, overlooking a serene lake surrounded by trees. The bubbling water reflects the greenery, creating a peaceful atmosphere for relaxation.

Home in Greenwood Lake

Stylish Lakeside Cottage with Hot Tub

Indoor spacesKitchenSkiing

Family- and pet-friendly home rentals

Apartment in New Rochelle

A cozy living area features a stone fireplace with an elegant mantel. A flat-screen television is mounted above, while a stylish gray sofa and two chairs surround a circular coffee table. Natural light is filtered through sheer curtains beside a decorative plant.

Cozy apartment in New Rochelle

FamilyIndoor spacesCondition

4.86 out of 5 average rating, 134 reviews

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

Indoor spacesKitchenParks

Home in Cold Spring Harbor

A light-filled living area features a comfortable sofa adorned with nautical-themed pillows. A wooden coffee table rests on a woven rug, while a stylish floor lamp and wooden chair enhance the space. The ceiling showcases exposed beams, adding character to the room.

Nautical Farm House on Working Farm with Animals

FamilyIndoor spacesTV

4.86 out of 5 average rating, 313 reviews

4.98 out of 5 average rating, 141 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

KitchenIndoor spacesAccess

Guest suite in Hastings-on-Hudson

The sleeping area contains two full beds with patterned bedding. A small couch is positioned beside the beds, accompanied by a side table and a kitchenette area in the corner. Natural light enters through glass doors leading to the outdoor space.

Adorable 1 Bedroom 2-Bed suite near NYC

KitchenFamilyShared spaces

4.91 out of 5 average rating, 148 reviews

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

Indoor spacesKitchenCheck-in

4.99 out of 5 average rating, 220 reviews

An open floor plan is showcased, featuring a cozy living area with a gray sofa and a wooden coffee table. A dining area with a round mirror and a six-seat table is visible, along with a kitchen equipped with modern appliances. Natural light fills the space.

Home in West Hempstead

Modern 3 Bd Spacious Apartment in PRIME Location

KitchenFamilyAmenities

4.93 out of 5 average rating, 634 reviews

A bright and airy studio space features a canopy-covered bed draped with sheer fabric. An ornate mirror and a small table with decorative items enhance the room's charm. Natural light fills the area through large windows, complemented by a cozy seating option.

Guest suite in Bayville

Romantic, Cozy and Private, 1 Block from Beach

KitchenIndoor spacesLocation

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 184 reviews

A serene pool area features a deep blue unheated swimming pool with steps leading in. A gazebo, softly illuminated by string lights, is nestled among lush greenery in the background. The natural landscape creates a tranquil retreat.

Apartment in Chester

Private Country Getaway

KitchenFamilyGetting around

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

Indoor spacesFamilyCheck-in

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 spacesFamilyCleanliness

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

Indoor spacesKitchenValue

4.87 out of 5 average rating, 119 reviews

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

Indoor spacesFamilyLocation

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

Indoor spacesKitchenCheck-in

4.9 out of 5 average rating, 537 reviews

An outdoor lounge area is framed by wooden beams, featuring dark seating arrangements around a small table. Soft lighting casts a warm glow over the scene, with landscaped greenery and vibrant flowers enhancing the ambiance. The resort-style pool is visible in the background, reflecting soft colors.

Apartment in Union

2 Bed Apt | Quick Access to NYC

KitchenFamilyCleanliness