Family-friendly holiday rentals in Port Chester

This airbnb is beautiful! It's clean, well-located, and comfortable. Anthony was very communicative. I loved the backyard access. I would happily stay here again.

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!

Paula and her place are absolute gems. Communicating with her felt like talking to a friend whose place I was going to be staying at, and it felt like that when we arrived as well. I loved the art and thoughtful touches in each room, and our large group felt cozy yet everyone had their own privacy. The space is actually much larger and more beautiful than the photos even convey! The private trails were stunning and magical— I walked barefoot on the carpet-like moss covered forest paths leading to a Stonehenge-esque clearing with giant boulders. The deck and outdoor space is lovely and has stunning views. So peaceful and quiet with some surprise owl and hawk sightings.

Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!

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!

Had an absolutely wonderful stay! Location is perfect and Jaime was incredibly friendly throughout!! He let me know that they had everything we would need.. but as a self-described obsessive packer I didnt listen. He wasn't kiding! They had beach chairs, umbrellas, and everything else you need for the perfect beach day. I brought an entire wagon of stuff and used one bag. It really is an awesome little find!!

We enjoyed a beautiful early spring stay on the farm with a group of 7 ladies, gathering for a chill bachelorette weekend in Cold Springs. The farmhouse was super cozy; great for cooking, crafting, games, tea time, outdoor wine picnics, star gazing at night in the hot tub and making friends with the chickens! A great retreat spot for groups with all the amenities!

This felt like you were just at home. Between the amazing host and their hospitality from beginning to end you would think you’re just visiting your aunt and cousins! Everyone was very pleasant and the house was the most beautify thing I’ve ever seen. I would absolutely recommend anyone who wants luxury in Brooklyn to stay here!

Viviana is a great host and very helpful. The apartment is very clean and well-organized. The apartment is especially quiet, which allows for great sleeping. Thank you for being such a wonderful host!

The place is wonderful, had a great cozy stay, the beds are comfortable. Would recommend if you’re looking for a place that’s close by all the restaurants and attractions.

Another great stay! I stayed 3 nights while visiting my son and his family. Apartment is clean,quiet and comfortable. Jennifer is responsive and helpful!

this home makes you feel right at home. plenty of room. great location. great host , very courteous. best place to stay if visiting long island. very safe neighborhood, short walking distance to shops, beach and LIRR station

Great place to stay while visiting West Point Military Academy. Highly recommended. Great host

If you want to relax and take in a gorgeous view, this is the place! The apartment is huge; you can really spread out. The two living areas have that stunning view over the Hudson. Looking at a map, we think there's a state park opposite the Airbnb, so there's no development, just trees on the hillside. The weather was closing in, so we didn't get the gorgeous sunset we'd hoped for, but you might. We did takeout so that we didn't have to leave the view. Brothers Fish & Chips was a total delight -- the fish was fresh and lightly battered. Very much like you get in England! And the hosts provided breakfast items, a real bonus. Two things to note -- commuter trains run between the property and the river (but below the level of the apartment) and Sing Sing prison is within view. We weren't bothered by either, especially since there aren't many trains at night and you don't see them from the patios. And driving along the prison road to pick up our takeout was more interesting than scary.

My husband and I had a great stay. James and Rose are super helpful hosts. It’s a great place to relax and enjoy nature. Walking distance to a lovely park they recommended with tons of hiking trails and very quiet.

Linda’s home is absolutely beautiful and unreal! First of all, it was extremely clean with great smelling sheets. Her home had everything you needed from coffee, seasonings, first aid kit, and even marshmallows to roast. My family and I had a bbq as well and Linda had a lot of cookware. We had sooo much space to walk and go on a hike right off the property. There is a little stream of water that connects to the pond which my little 4 year old loved. The horses were a lovely addition and we loved hearing the rooster during the day. We will certainly be returning because a weekend was too short to explore everything. I highly recommend! Thank you again Linda!

We had an amazing stay at Sally’s place in Bethel! My fiancé and I visited CT for the first time to celebrate my birthday and go to a convention nearby. This cottage was perfect for the two of us. The host was very responsive and accommodating as well! The cottage was in pristine condition, the house manual was very easy to follow, the recommendations were great, the scenery was out of a movie, and my favorite part was the hot tub in our restroom which was perfect after a long day! We had a great time and would love to come back again! Thanks for your hospitality Sally! ☺️

Robert was an awesome host! Super easy to communicate with and made check-in and check-out a breeze. We even got to meet him he made balloon animals and did magic tricks for our kid, which was the sweetest thing ever. Seriously such a down-to-earth, kind person. The neighborhood was quiet, cute, and felt really safe. The house was beautiful and way bigger than we expected! We had everything we needed and felt totally at home. Definitely planning to book with him again!

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!

Delighted we picked Martha’s place for our stay in Queens. The place is exactly as described. Clean, comfy, and in a good location for exploring the city. Would def stay again if visiting NYC.

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!!

The space is adorable, and we loved the history of the rental and the community. The location was perfect for us—close to everything and secluded all at the same time. Also Jeff is an amazing host and made us feel welcome/at home. The next time we have to head to NY for a family visit we will definitely try to stay here again.

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