Family-friendly holiday rentals in Port Chester

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!

Indoor spaces · Kitchen · Amenities

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.

Kitchen · Indoor spaces · Cleanliness

Charming 3BR Home - Quiet Stay, Close to NYC

Welcome to your White Plains retreat- a beautifully renovated townhouse designed for convenience and a relaxing stay. Perfect for families or small groups, the home features a modern kitchen, three cozy bedrooms, and inviting spaces that truly feel like home. Just a 12-minute walk to North WP Station, you can reach Manhattan in about 45 minutes while still enjoying the restaurants, shops, and charm of Westchester. As Airbnb Superhosts, we’re dedicated to making every stay seamless and memorable.

Kitchen · Indoor spaces · Parking

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!

Kitchen · Indoor spaces · Value

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.

Kitchen · Family · Checkout

Flex Comfort Apts of Greenwich #1

Flex Comfort Apt #1 is 1 BR / 1 BA and sleeps 4. Apt #1 is the bottom floor ('Basement') of a 3 apt 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 spaces · Family · Quiet

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.

Indoor spaces · Kitchen · Getting around

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.

Indoor spaces · Kitchen · Outdoor spaces

Overlook Cabin in downtown Greenwich CT

Last house on a private road, parking onsite if available, conveniently located walk to train station, Greenwich Avenue in Greenwich CT to the ferry, Sherman Park for beach access. Travel to New York City in 37 minutes with the Metro-North Express train. We are at one of the highest points on the Greenwich Coastline. You can hear the sounds of life: from church bells ringing, the train to NYC and Rt 95 traffic, NO SMOKING NO parties NO events Sorry NO PETS service animals always welcomed.

Kitchen · Family · Walkability

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.

Kitchen · Family · Hospitality

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Welcome, to newly renovaded small studio for one guest with private entrance, bathroom, small kitchen with microwave, coffee maker and refrigerator. Off the street parking, you have your spot reserved during your stay. One mile from I-95, walk to shopping and restaurants, five minutes drive to Stamford downtown.

Indoor spaces · Family · Wi-Fi

Bright Stylish Chic 4BR 4BA Home

Welcome to this sunny, chic, spacious 4BR, 4BA North Stamford country house with lots of character and a huge backyard. Great for families. Light & bright, open flow, skylights galore, deck and grill, spacious playroom. Large primary bedroom suite. Just 1 hour from NYC.

Family · Indoor spaces · Wi-Fi