Family-friendly vacation rentals in Cutchogue

This was the most beautiful house in a private area in Wading River. It offers peace and tranquility and lives up to its name of Zen Retreat. It was exactly what we were seeking. Conveniently located near parks, farms and wineries I would definitely go back to Brian’s AirBNB. He was an excellent host and very responsive to our needs. Thank you Brian.

We had a wonderful weekend. Great place to stay. Would recommend it highly.

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!!

This was a great find for a long weekend! It was perfect for our dog as the front- and backyards are fenced in. Wonderful kitchen, great pool and close to town which made for a perfect stay. Cindy gives good recommendations on restaurants and activities and is very responsive if you have any questions.

We brought our three adult children here to reconnect and explore a new beach town, and this home was the highlight of our trip. It offered the perfect mix of fun and relaxation—truly the most amenities we've ever had at an Airbnb. We enjoyed nightly game competitions in the incredible game room with golf simulation, ping pong, Pac-Man, racing games, and more. The basement had board games and a basketball shootout we loved. The pool, hot jacuzzi, and dinners on the deck made for relaxing, memorable evenings. Ann Marie was kind, responsive, and a joy to work with. Her eye for design made the home feel like something out of a magazine. The beds were super comfortable, and the natural light throughout the home was beautiful. Thank you Ann Marie, for entrusting your incredible home to our family. The memories we have made are priceless and we are very grateful to have had this amazing opportunity! Our only regret was not getting around to do the Karaoke machine-Next time!

This spot was a great find. Hadn't been to Shelter Island before. I found the location super convenient. Literally every place I went was 5 mins on GPS from her house. She was very clear about everything, responsive to emails, and everything was as described, however the pictures don't do it justice. Beautiful home and pool, people came to clean the pool early one morning during the stay and were not disruptive at all. There were beach chairs, umbrellas, pool floaties, games, netflix, literally everything you could want or need. Loved our stay!

Kathy was an amazing host. She was communication and helpful with everything we needed or asked for. Her place was absolutely incredible. Would definitely stay again!

We loved our stay at Chandra’s place, it was peaceful, super comfy and was close to everything we needed. It was great to enjoy a few runs locally and come back to the private garden and hot tub in the evening. The property was beautiful and well stocked with towels, soft bedding and kitchen equipment. I’d love to come back again in the future

Clean, spacious, private basement apartment with some natural light. Very comfortable bed. Lovely backyard. Quiet, green residential neighborhood. Within 10 minute driving distance from Port Jefferson town center.

This is our second time staying here, conveniently located. Very comfortable accommodation for me and my family. Will definitely stay here again!

This place checked all the boxes. Very clean and comfortable home and a short uber ride to downtown Sag Harbor. Nice big yard for relaxing after a long day on the boat. Will definitely stay here again. Great host and a great place

Beautiful property. John is a great host and made us feel welcome. Loved the park and beach nearby. Our dogs had a blast. Wish we could have stayed longer and would love to come back.

Victor and Kim were gracious and amazing hosts. I was celebrating my birthday and they even had a card, a bottle of champagne, red wine and fruit. It was such a wonderful surprise! The house was so beautiful and the beach is just outside! The kitchen was fully stocked with everything one would need to cook for a family; there was a convection oven! We loved using the grill as it was memorial day. Bathrooms had rain showers. Beds were so comfortable and it was truly wonderful to wake up to a beautiful sunrise and to just listen to the waves from the deck or even the living room. We spent a lot of time outside, on the beach. It was home away from home.

We had a great time at Betsy's place. The home was beautiful and had an artistic charm, even better in person than in the photos. The location was perfect - close enough to town and yet felt private. We had a great time and would highly recommend this place. I'm looking forward to being back here in the future.

We were greeted by walking through the gate to the backyard in a rhododendron bush in full bloom. It was absolutely gorgeous. Everything from walking in the door to the Airbnb apartment to settling into the very comfortable bedding we had a really lovely stay, and I would definitely return for future trips. Michael helped us find a beach that didn’t require a local sticker that was perfect!

It was so comfortable and peaceful. We had a great time exploring nearby beaches and hikes. We would definitely stay there again.

Marta could not have been more accommodating! She was responsive and provided everything we needed. She even went the extra mile and insta cart-ed garbage bags and paper towels when we ran out. She could not have been a kinder host! We had the best weekend and would HIGHLY recommend staying at Marta’s place! We will definitely be back!

Gabby’s apartment is exactly as described. It is in a great location. Very close to Stoney Brook Village. We enjoyed walking to get our morning coffee. The apartment was very well stocked and spotless. Gabby thought of everything we could have possibly needed. We hope to be back next year!

We had an amazing stay at Michael’s Airbnb this past weekend! The space was exactly as described—clean, cozy, and well-equipped with everything we needed. Michael was a fantastic host: super responsive, thoughtful, and made us feel completely at home. The location was perfect for a relaxing getaway, and the setting was even more beautiful in person. Would absolutely stay here again—thank you for a wonderful experience, Michael!

Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.

Absolutely loved our stay and the hospitality of the host, Kate. The house was very nice and the property is very private. Highly recommended! Thanks Kate!

Yvonne's place is wonderful, we spent six days there on a family vacation to celebrate a graduation and it was a perfect spot for a crowd. The description and pictures are spot on (maybe even better) and the place is very well maintained. The weather was not great - so we landed up staying in more than we anticipated and this was a great spot for that. The kitchen is well stocked, having a barbecue really helped, and the large windows and skylights kept us connected to the outside. Yvonne was also highly responsive in case we needed anything. Highly recommend.

Absolutely wonderful stay! Christine was extremely helpful and responsive. She was so clear with instructions and everything was exactly as described. The house was very clean and exactly as described. The yard was also very big. Perfect for a weekend getaway as it was close to everything. Highly recommend if you are looking for somewhere to stay near Hampton Bays. Would absolutely return.

Benjamins place was a wonderful stay for our family. Coming from the City it was amazing to have so much grass with peace and quiet. It is a short walk to the Main Street and Sag Harbor downtown. We had planned to go out and enjoy some activities during the couple of days we stayed but instead found the place so relaxing we spent most of it in the home. The separate house was nice for a master bedroom and quiet. We would highly recommend this house to anyone wanting to have a relaxing and quiet vacation in the Hamptons near Sag Harbor. Hope to be back again!