
Family-friendly holiday rentals in Port Chester
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Port Chester

Total holiday rentals
Explore 20 holiday rentals in Port Chester

Nightly prices starting at
Port Chester holiday rentals start at $208 AUD per night before taxes and fees

Verified guest reviews
Over 720 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Port Chester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Port Chester rentals

4.9 Average rating
Port Chester stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Port Chester
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Flex Comfort Apts of Greenwich #3
Flex Comfort Apt #3 is 2 Bedroom / 1 Bath and sleeps 4. Apt #3 is the top floor with the best light and nobody above. Private Parking & Entrance. Great mattresses, linens, big screen smart TVs, multiple desks, and clean. Well stocked kitchen to put on 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 spacesFamilyDecor

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!
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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.
Indoor spacesKitchenComfort

Cozy Guest Suite in Greenwich, 1mi from train
A light-filled studio with private entrance in a newly renovated home. Nestled on a very quiet street, it offers a queen size bed with private bathroom and lounge space (sofa bed) . The space small kitchen amenities include a refrigerator, coffee machine, kettle and microwave, Wi-Fi and private bathroom with shower are additional features. Other things to note As we are a young family looking for total quiet during your stay? We may not be the best hosts for you. Otherwise, please reach out!
KitchenFamilyValue

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!
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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.
Indoor spacesKitchenParking

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.
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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!
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Cozy 2 BR Greenwich Apt. with easy access to NYC
Cozy two bedroom apartment on a quiet street in Greenwich with brand new appliances. Walking distance to Metro North train station, beach, park, tennis court, pickle ball court, restaurants, shops. Just 38 minutes from NYC. Few minutes drive to downtown. Fully stocked kitchen and laundry with everything you may need. Living room with 65" Smart TV. Master BR with 45" Smart TV. The apartment is professionally cleaned & sanitized up to CDC guidelines & inspected before each stay.
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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.
FamilyIndoor spacesValue

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.
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Charming Retreat in North Stamford
Whether you are in town for business or simply to enjoy the peace and quiet of the suburbs, WELCOME TO OUR HOME! A great getaway suite in perfectly located North Stamford home, just 60 minutes away from New York City. Please be advised, this unit as pictured is on a lower lever and part of our main family home.
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Popular amenities for Port Chester family-friendly rentals
Family-friendly home rentals with a hot tub

Bedford Paradise Getaway | Hot Tub | Town Center
FamilyIndoor spacesWalkability

Coastal Villa Suite pool•sauna•gym•theater•beach
Indoor spacesKitchenShared spaces

Magic Red Barn with Heated Salt Pool (opened now)
FamilyIndoor spacesValue

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

Tuxedo Hilltop Retreat with a Large Hot Tub
KitchenIndoor spacesParks

Spacious Historic Loft • 20 Min to NYC & EWR
FamilyIndoor spacesAmenities

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC
FamilyKitchenAccuracy

Business+Family Friendly Balcony Jacuzzi Free Park
Indoor spacesKitchenHospitality
Family- and pet-friendly home rentals

Your Modern Guest Wing Near NYC
FamilyKitchenSleep quality

Bright & Modern Victorian in NY Suburbs
Indoor spacesFamilyAccess

Gem by the water+ firepit and all fenced backyard
Indoor spacesKitchenLong stay

HighLineHarbor Flat2BD|Train2NYC|HarborPointAccess
Indoor spacesFamilyTV

Woven Winds Retreat
KitchenFamilyAir conditioning

Walk to Greenwich Ave [KING bed] BEST Location
KitchenIndoor spacesBarbecue

5BR Beach House, Water Views, Game Room, Backyard
FamilyIndoor spacesNearby

Family Cottage with 4 King Beds and Fire Pit
FamilyIndoor spacesParks
Family-friendly home rentals with a pool

Peaceful Light-Filled Guesthouse salt pool/sauna
Indoor spacesFamilyDecor

Charming Historic Cottage in the Redwoods
FamilyIndoor spacesPets

Private Guest Studio
FamilyIndoor spacesQuiet

Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Indoor spacesKitchenAccuracy

Private Murphy Bed Style Studio
FamilyIndoor spacesValue

E and T Getaway LLC
FamilyIndoor spacesView

Midcentury Modern ZenHouse Sculptor Studio
Indoor spacesFamilyBreakfast

Great Family Times in this 5 Bedroom House
FamilyIndoor spacesBeach
When is the best time to visit Port Chester?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $425 AUD | $444 AUD | $444 AUD | $430 AUD | $457 AUD | $473 AUD | $415 AUD | $420 AUD | $415 AUD | $418 AUD | $509 AUD | $416 AUD |
| Avg. temp | 1°C | 2°C | 6°C | 12°C | 18°C | 23°C | 26°C | 25°C | 22°C | 15°C | 10°C | 4°C |
Destinations to explore
- New York Holiday rentals
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- Times Square
- Central Park Zoo
- Mountain Creek Resort
- Yale University
- Jones Beach
- Columbia University
- Yankee Stadium
- American Dream
- MetLife Stadium
- New York City Center
- Rockefeller Center
- United Nations Headquarters
- Empire State Building
- Bear Mountain State Park
- Bryant Park
- Barclays Center
- Citi Field
- Statue of Liberty
- Grand Central Terminal
- Brooklyn Bridge
- Radio City Music Hall
- Astoria Park
- Fairfield Beach
- Thunder Ridge Ski Area





