Family-friendly holiday rentals in Port Chester

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!

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!

My family of 8 adults needed a place to stay near a wedding at Glynwood. This wonderful spot was minutes away from the farm and town. The number of bedrooms and bathrooms gave everyone the privacy desired while the well equipped kitchen and living rooms had plenty of space for gathering. The house and land are beautiful, including the trail. Paula was easy to communicate with and my whole family felt comfortable and happy with the spot. Highly recommend!

The house was everything it advertised, and Anca was a wonderful host, she was helpful and responsive. The kitchen was spotless and well stocked, best stocked kitchen I’ve ever experienced in an AirBnB! The appliances worked perfectly, the bedrooms were comfy, and the bathrooms clean and nicely finished. Lastly, Anca’s house had some of the nicest touches I’ve experienced, like cell phone charging cords in many rooms!

Fantastic absolutely amazing experience. Jaime was beyond great when it came to professionalism and kindness and responsiveness. Super clean beautiful apartment didn’t miss a trick when it came to anything you might need. This was a top-notch experience. Amazing customer service, beautiful location. Beautiful pool and spa overlooking the ocean We will definitely be back.

Roma was very sweet and welcoming showed us where everything was. We even got to meet beautiful grandchildren. The space was very beautiful and glad it offered parking. This will definitely be saved as s favorite for future bookings

Lisa’s place was fun and relaxing for our family. Great place to relax and unwind all while being close to the great areas we visited. Lisa was a great host ❤️

Linda is such a great host! She is SUPER organized from the very beginning giving us clear instructions about the check in, the rules at the house, leaving printed version of all of that in different sides of the house, and even to the way she organized and provided everything we ever needed at that house. And the house itself is soooo gorgeous and peaceful I felt right at home. The only flaw is that it has bad reception in the area since it is surrounded by woods. But Linda provided us with strong wifi in the house, so I guess that settled it.

We stayed at Sarah's place during graduation week at West Point. The house worked well for our group of 8. We loved having such a well equipped kitchen and the comfortable beds. The yard is beautiful with a great patio and, grill and fire ring out back. We saw a lot of deer and the view of the Hudson River is fantastic. Sarah was a great host! I definitely would recommend staying here!

Jacquelyn was very responsive, proactive, provided clear instructions and her place and linens were very clean! If you love farm animals, you’ll enjoy this place even more as she allows you to visit her farm.

Peter's place is THE perfect stay for a couple (plus dog) planning a visit to Rockland County. The cottage is extremely clean and incredibly cozy. The surroundings are beautiful, with the property well set back from the road and bordering Harriman State Park. Suffern and its restaurants aren't far and there's easy access to the Palisades Parkway to go anywhere else nearby. I grew up in the county and visit my parents on a regular basis. Any time I can't stay at their home, Peter's place will be my go-to from now on.

Really enjoyed our stay at this peaceful farm. The location was very convenient to Bear Mountain State Park / the Appalachian Trail. The sound of the frogs at the nearby pond and the friendly horses really make this place a gem. Would highly recommend for a relaxing getaway!

Brian's place was exactly as described, and a perfect home base for our family of 3. Very clean, comfortable, and in a wonderful part of Brooklyn. Felt at home -- we would stay again!

We loved staying at Great Gull. The house easily housed our family of 5 with plenty of indoor and outdoor spaces to relax. The home is clean and well stocked with kitchen basics (including coffee and spices) for cooking and the bathrooms included toiletries. Convenient access to the beach - we loved hanging out in the private back yard and patio. We would definitely stay here again!

Thanks Peter & Jess for a wonderful stay. The house is beautiful and was a perfect homebase for us in Brooklyn. Thanks again!

We really enjoyed our stay! The Airstream matched the photos and listing perfectly and is tucked in a quiet, wooded location. We were able to walk to the restaurants, small shops and the train station. Highly recommend this spot for anyone craving the nostalgia of 80s camping.

My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.

What a great stay ! Robert is fantastic, welcoming and thoughtful throughout our stay! My son wanted to play his guitar and needed a few strings Robert went above and beyond by having those strings and giving them to him, such a thoughtful gesture. Place is great has everything you need! Turn the AC on and the provided fans and it’s plenty cool enough. Backyard pool is beautiful! Would definitely recommend this to friends and would love to stay again!

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!

Had a very enjoyable time during my stay. Hosts were very helpful, friendly, accommodating, and responsive. Gave lots of great recommendations for dinner spots and shopping. The house was very comfortable, clean, and cute. Will definitely be booking again!

The place worked perfectly for what I had needed. Travel a lot for work, and this time my wife and son came to visit for a few days of the stay. Host was very nice and helped us with accommodations and recomendations of local eateries. Very much enjoyed our time here, would stay again.

Charlotte's place was perfect for my group of friends in town for a wedding. We loved having the pool and a great back yard to spend some time outside and the open kitchen/living room was great for hanging out together. It was a little over a mile walk to get into downtown Fairfield but the house is centrally located and in a great neighborhood. Would stay here again!

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.

It was comfortable, very roomy, and cozy. There was good shared space and good privacy. The grounds were lovely, there was a great pool, and it was very convenient to so many good things to do in the area. It's one of our favorite rentals to date!