Family-friendly holiday rentals in Wainscott

We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

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 wonderful weekend. Great place to stay. Would recommend it highly.

Amazing! We really enjoyed our stay. Abby and David are extremely hospitable, responsive, and friendly hosts. The house is beautiful, clean, and well-located. The pool, hot tub, desk, and back garden are even larger and more beautiful in real life. We will definitely be back. Thank you Abby and David!

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 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

I thoroughly enjoyed my stay in the Ironwood. It was a very a unique experience. The trailer was comfortable, cozy, clean, and looked exactly like the photos. Issac was a fantastic host. Looking forward to returning!

🌟 A Perfect Hamptons Getaway – Highly Recommend! 🌟 We had the pleasure of staying at this beautiful Airbnb in the Hamptons for two days, and it was everything we hoped for and more. The home is a stunning blend of modern elegance and cozy charm. The interiors are tastefully decorated, creating a warm and inviting atmosphere. We especially loved the spacious living areas and the well-equipped kitchen, which made meal preparations a joy. Our host was exceptional responsive, accommodating, and genuinely kind. This Airbnb exceeded our expectations in every way.

This was now my second trip at Gary’s Southampton cottage, and it was equally as fantastic as my first! Inside, the place was spotless, and on the porch is a grill as well as a fireplace. We took advantage of both, grilling almost every day, and capping our nights with s’mores by the pit. Gary’s cottage is in the perfect location! Downtown is only a 15 minute walk away, where you will find plenty charming boutiques as well as a CVS and some grocery stores for your convenience. The beach is only 15 minute walk away as well. Luckily, Gary is very generous and provided us with bikes, so we were able to cut those times in half. He was also very generous and allowed us to use the pool and hot tub when the main house guests were gone. Even when there are main house guests, the cottage is tucked behind a large hedge, giving you separation and privacy. Overall, fantastic place and fantastic host, highly recommend!

Jason was great, very responsive and helpful with my mom. Dog friendly, and there are pet pigs and chickens, too!

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

Amazing place!! Great location, beautiful yard. Would absolutely stay here again.

Lovely place for a long weekend with family! The house was pristine, up to date, charming, and all the linens were fresh and clean. It was very well stocked with kitchen essentials and books and toys for kids. Location also prime with a private beach a 10 min walk away. The only minor issue we had was an issue with the pool heating (it being the 1st pool weekend of the year) but this was sorted out promptly. Would happily stay there again!

I stayed at Mary's rental with my sister's family including a 4yo and 6yo, as well as my 72yo mother and the house was a perfect fit! The downstairs bedroom and full bath were perfect for mom to avoid the steep stairs, and the house was well equipped with a ton of kids books and some toys. Proximity to town was the highlight, we were easily able to walk with the kids which was perfect since the weekend was too chilly for the beach. Mary was responsive if needed but the house is well stocked and easy to navigate so we felt at home right away. I will absolutely be renting from Mary again!

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.

We had the most wonderful and peaceful fall weekend at Brooke’s cozy cottage to celebrate our anniversary, and it was truly unforgettable! The cottage itself is beautifully decorated and felt like a warm home away from home. Brooke went above and beyond to make our stay special, leaving us complimentary champagne and wine to kick off our celebration. The location was perfect for enjoying the crisp fall air and stunning foliage, providing the peaceful retreat we were hoping for. We can’t recommend this place enough and will definitely be back for another 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!

Everything was perfect for our girls weekend. This is the 3rd time we’ve used Laurie’s house and there’s obviously a reason we keep coming back. Can’t wait to go again.

Loved the stay! Exactly what we thought it was - extremely convenient and cozy. Plenty of beaches to walk to and the food options were plentiful. Would definitely stay again.

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.

We absolutely loved our stay at Milton & Megan's Montauk house! It was perfect for a group of 4 (2 couples) there for a 4 day trip. The house is very quiet & peaceful, with lots of outdoor space, but also very walkable to town. The house was super clean, and everything was very easy to find. The bedrooms had lots of closet space, the TV was easy to set up, and all the amenities listed on the website were accurate. We'd love to come back again and stay. Thanks!

John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.

We had a great time at Mark’s place! The backyard was quiet and beautiful - it was the perfect relaxing weekend for our group. We’d love to stay here again!