Family-friendly holiday rentals in Port Chester

We had a wonderful few days in Anthony’s apartment in Williamsburg. The apartment has absolutely everything you need and is extremely convenient to subways, coffee shops, restaurants etc. It’s also tastefully appointed and well designed. I wish the weather had been warm enough to spend time in the backyard. It’s beautiful! Anthony is super responsive and welcoming! We enjoyed our stay immensely and will be back!

We had a wonderful stay at the Lake House. The house was beautiful and large enough for my family of 6. We enjoyed the hot tub with views of an icy lake. Beds were comfortable and bathrooms were clean and fresh. We went bowling and found great restaurants in nearby by Warwick. We would love to return soon!

We wanted a place close to home in NYC that felt like it was a thousand miles away - this place fit the bill. My city pup became a country dog and my son, boyfriend and I all felt our blood pressure drop. The woods in the back were pristine and the teen loved the hot tub on a cold cold night. Thanks for hosting us. I hope we will be back in warmer months.

My family was in town for a funeral, and we were able to book Victoria's home and save versus booking multiple hotel rooms. The location is minutes of I-95, so the home gave us a nice, central home base with a kitchen to get to everything and feed the kiddos between events. While we weren't looking for a beach trip - we were able to walk to the local beach and enjoy it with our young kids for a few hours over the weekend. The home was clean, comfortable, and worked perfectly for us. Communicating with Victoria was very easy, and check in/out was a piece of cake as there is a lock box on the house. If I need to bring the family back to the Stamford area, we'll definitely want to stay at Victoria's home again! Thanks!

This was our second time staying at this home, and just like the first time, everything was perfect. The place is exactly as described—clean, comfortable, and well-equipped with everything we needed. It suits my family, who visit me every year from abroad, perfectly. The location is convenient, the neighborhood is quiet, and the hosts are absolutely lovely—friendly, responsive, and thoughtful. We truly feel at home here and will definitely be back again. Highly recommend!

This place was perfect for a city getaway! Me and a couple girl friends went up to the cabin for the weekend and it was so so fun. A beautiful home, and a gorgeous property. Whenever I had questions there was always a very swift response, the grounds keeper is an absolute angel and the kitties running around outside are so fun. Would totally come back!!

Everything is as beautiful in person as it is in the photos. A very cozy home that was very thoughtfully stocked with things you might need. Roma was a very sweet and accommodating host and made sure to leave me with some snacks and a bottle of wine after giving me a quick tour. A jacuzzi and a parking spot is a such a gem in Brooklyn. Would definitely book again and highly recommend!

We had a lovely weekend at Claudine's. The property is serene. The house is very well equipped and comfortable. We also loved having the sauna. We wanted to grill, but propane was not included in the grill and incurred an extra cost or we had to bring our own tank. For the price and nature of the house, including something like this seems fair. All in all we had a wonderful stay.

Johnny and Amy were amazing hosts. The instructions to park, enter and get in were very well written out before our arrival and check-in was seamless. And once we were there, the place was beautiful, cozy and exactly as described. Our kids loved running around outside in the grass and exploring the outdoor fire-pit. If you want peaceful mornings, laying in bed, watching the wind rustle the trees and listening to the birds sing their morning songs, this is a place for you.

We thank very much Bob and François for their apartment. It is well located for easy access to New-York. Grove Station (metro station) is near the apartment, to go easily to New-York through the PATH (Port Authority Trans-Hudson. The PATH offers twos possibilities to go to New-York: to World Trade Center or to 33rd Street if we want to go upper into Manhattan. The street is quiet, without noise during the night. A grocery store is open late at night, between Grove station and the apartment.

Perfect little Jersey City studio right in the heart of the city.

Great spot in Park Slope! Would definitely stay again.

Dan and Jill’s place was a peaceful little gem with a stunning view from living room windows. There are multiple outside spaces to relax. The inside was absolutely spotless and decorated very nicely. Lots of plants give it a zen feel. The kitchen was beautiful and nicely appointed. Extra effort is made with the coffee amenities. Would stay again ! 😊

Perfect stay in the coziest cottage! Rose & Jamie were amazing and super helpful and made us feel right at home.

Denia’s place was really great! We stayed there for a week with friends and it was a nice experience. There’re buses to NYC at a 5 min walk, as well as a bunch of services and restaurants near the place. Denia’s instructions were very clear, and I would recommend it to friends.

Tony’s cabin is a perfect lakeside escape. The space is clean, well-designed, and bright with natural light. The fireplace is huge and beautiful. The large windows overlook the lake. A deck leads down to the little lakeside area where there are stand-up paddle boards and kayaks. The neighborhood is quiet and walkable with a nice beach area about 10 minutes from the cabin. Cold Spring is 20 minutes away and has yoga classes, great massages, coffee shops, and restaurants. There are seemingly endless hikes within 20 minutes drive of the cabin. We hiked a different park every day. We had the best time relaxing in the cabin and enjoying the beautiful surrounding area!

When my plumbing went rogue and turned my floor into a squishy disaster zone, I needed a place to crash that wasn’t half underwater. Enter Sally’s place—a true oasis in my time of crisis. First off, this place is so nice that I briefly wondered if my house was even worth saving. It’s cozy, beautifully decorated, and so clean. The bedroom and bathroom are upstairs, making me feel like I was living the high life—literally. The bed? Like sleeping on a cloud. The view? So peaceful I considered writing poetry. Bottom line: If you need a place to stay, stop scrolling. Just book it. But be warned—you may never want to leave.

I booked this stay for my mom and her dog. Robert was a great host and very understanding and kind. My mom felt comfortable in the space and enjoyed her stay in Huntington 😊

Gaby’s place was clean and comfortable! She is very kind and it was exactly what we needed for the week. Her check in instructions and directions were thorough and the home is in a beautiful area. Already have our next stay booked :)

We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

We had an amazing and relaxing time at Igals beautiful house. The house is set back away from the street for the ultimate private get a way. The kids loved the pool Wich was very refreshing and cool for the hot summer days. Igal was extremely responsive and accommodating to all of our needs! We will definitely be returning in the future:)

lovely place to stay in. would come back again. 10-15 minutes walking to the subway which gets you everywhere. even faster if you take the bus right around your corner. really helpful with recommendations and tips before and after we arrived

Great home and host. Responsive to inquiries. Would recommend!

Beautiful area. The apartment was comfortable, modern, and enjoyable place to rest after a long day of sightseeing. Really enjoyed the heated floor in the bathroom. Our host was friendly and helpful with area attractions and places to eat. Would rent again.