Family-friendly holiday rentals in Cutchogue

We had an event nearby and Brian’s place was a great base for us. Lovely and peaceful neighborhood. Brian was super responsive and reached out to us when the house was ready(before the official check-in time). Would def recommend to anyone!

We had a fantastic girls weekend in Southampton and loved Anthony's cottage. It was so beautifully decorated and cozy. We throughly enjoyed mornings with coffee and books in the sun room.

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.

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.

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!

We had such a wonderful stay at Ann Marie’s Airbnb! From the moment we booked, she was incredibly kind and responsive, making everything so easy and welcoming. The house itself was spotless, beautifully maintained, and had every amenity we could possibly need — it truly felt like a home away from home. The location was perfect — close enough to town that everything was easily accessible, but just far enough out that we avoided all of the typical Hamptons traffic. We even walked around the neighborhood every morning! We couldn’t have asked for a better balance of convenience and tranquility. Highly recommend this stay, as someone who frequents the hamptons — we’d come back in a heartbeat!

We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

Hi, we had a great stay with plenty of space for all of us. We all loved the fresh flowers on the living room table. The roses were a beautiful touch! The place was very clean to which my mother-in-law said it at least 4 times a day! LOL The bedrooms were set up so neatly when we arrived (very impressive). The kitchen had all the necessary utensils we needed and more. Great weekend! Thank you.

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

Mike is a great host with helpful recommendations and plenty of advice. The house is amazing. Well located, calm, clean and so convenient. The pool is huge and very deep. Everything is perfect. Felt like at home. We will be back

I had a very nice stay at the Rex. It is dog friendly and very clean. Although my space was private, there are other rentals nearby and it had a camp like feel. I would stay there again if need be.

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.

Had an amazing stay with my business partner. Farms around the area and proximity to multiple Hampton towns was ideal(5 mins from Southampton). Great stay, 10/10 recommend.

We had a fantastic stay! The home is exactly as described and the backyard was beautiful. We really enjoyed being able to walk to the private bay beach and utilize the yard space. Petra was very quick to answer any questions. We will be back!

Staying at Amy's place was perfect for my friends and I while we're out on the North Fork for a wedding. Amy was very responsive with any questions we had. We were all very comfortable in the main living area as well as our bedrooms. The house was conveniently located to the wedding venue and my friends were also very happy that it was located near some pickleball courts. Thank you Amy for a wonderful stay.

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!

Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.

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.

Christine's place was nice and clean! We especially loved the fire pit and the pool. Upon arrival of the AirBNB Christine was waiting to meet us and show us around. This was something that was new to me in my AirBNB experience, but it was honestly so nice and so was she! Christine let me know that I could communicate with her for anything that was needed and asked for recommendations to make her place better. This place was so well-equipped, close to everything and it comfortably fit me and my 6 other friends! I would definitely book again with Christine.

Ben is a super host. His home is absolutely beautiful and well managed. His thoughtful recommendations and well timed check ins and reminders were the height of polished professionalism. We felt right at home, down to the bins of toys in the living room that our toddler and baby played with every day.