Kid-friendly holiday rentals in Wainscott

The house was clean, well-decorated, had all the things we needed, and private, with a long wooded lot leading down to the bay. We women friends were totally comfortable there. When we couldn’t find the entrance to the driveway off the main road, she stayed on the phone & directed us until we found it. Excellent choice!

We had the most beautiful weekend stay at Tim’s home! Everything is accurately described and the pool and hot tub were amazing!! All the beds were very comfortable. Was perfect for a 5 girl weekend getaway!! Tim was incredibly communicative and checking in was a breeze. The location is PERFECT in East Hampton!! So many amazing restaurants and bars nearby. 100% will stay here again for my next Hamptons trip. Thank you so much Tim!!

our family enjoyed our time. Thank you!

Neha is surprisingly super prompt and helpful with her responses. Her place has beautiful views, is calm and easy to locate. The furnishings are great too

Perfect house, exactly what we needed and so close to everything. Will definitely come again! Also Dan was an amazing host and super responsive and helpful!

I do not even know where to begin.We had a last minute change from our other booking and was completely stressed but Harris came in and saved the day with making it so easy for us to book his house last minute.From the minute we arrived to the personalized note with fresh flowers to having every product we needed in the bathrooms .The home was beautiful and very homey and enough space for all of our guests .The location was fantastic and we can’t wait to come back .Harris was the best host and my daughter had the best week .If you are looking for a fabulous house with a great location look no further .Harris ,we can’t thank you enough.We will definitely be back .

Great location, private and comfortable. Close to wineries and breweries. Very clean and convenient. I highly recommend.

Lovely setting in the woods. We loved the layout, including many windows with beautiful views. Quiet neighborhood that is very walkable. Seeing baby deer in the spring was an unexpected bonus. Spacious bedrooms with extremely comfy beds. Host responded quickly when we had an issue. The private beach is a fantastic feature and easy to access. Check in and check out were super easy.

We had a great weekend at Nicholas’s place. It was very peaceful in the woods, and we enjoyed using the record player and looking through the books spread throughout the studio. Nicholas was very responsive when I texted with questions and we used his provided recommendations to find breakfast and dinner. We’d definitely stay here again!

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!

Sally was super helpful and responsive. Had a wonderful stay!

It was such a pleasure spending a weekend in Claire’s studio. The studio is very clean and comfortable, and my wife and I particularly appreciated the kitchenette, which allowed us to prepare a dinner one night and make our own pour-over coffee in the morning. We also loved hearing the birds as we woke up in the morning. And the location is terrific—an easy walk to the Southhold town center and a quick drive to other surrounding attractions like Greenport, nearby beaches, and wineries. Highly recommend!

Great place , nice people , very commucative, place has everything you need , clean , and felt home , definitely will come back again for great experience

Wonderful and cozy apartment! We were in town for a wedding and needed a clean and safe space to make home base. This was perfect. Would absolutely stay again!

Great venue. Hope to be back next year!

patti was so kind and welcoming! check in and check out was smooth and made easy with how communicative patti and her co host lily were. the room was perfect for two people and incredibly clean. had everything we needed. Pattis recommendations for food and activities were great and although the weather wasnt amazing the bay beach being so close was so convenient for a nice walk :) Would definitely come back given the opportunity!

The Beach Plumb was lovely! Everything was as advertised. The distance to town and the beach, the spacious layout, and the amenities are among the things that made our stay great

Mark's place was exactly what I was looking for to ring in the New Year in style, comfort and complete relaxation! I was able to start each day with a quiet cup of coffee and then head directly to the beach for a long morning walk (just a short drive away). Montauk Manor is an absolute hidden gem for a winter break and the indoor pool and hot tub are a rare find in the Hamptons. Check-in/out could not have been any easier and the Manor staff are wonderfully welcoming and friendly. There were still a good number of local shops open, including Left Hand Coffee. 100% recommend for all seasons and will eagerly book again!

We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace

Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

We had a great stay! Instructions were clear and the home had everything we needed.

Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!

You can not beat this location - quiet private beach right across the street, nice pool and about a 20 minute walk to town or super short car ride. The place is clean, as pictured and John was great to deal with. Will definitely be back!