Holiday rentals with a pool in Wainscott

Beautiful, clean property! Bedrooms were spacious and the beds were so comfortable. We enjoyed the hot tub while the snow fell...its a perfect weekend getaway house. I wish I could come back in the summer to enjoy the pool. AJ was very responsive and provided easy instructions for easy check-in.

I stayed at Ashton's place by myself on a visit to see my parents, who also live in Springs. It was everything I could have hoped for. So peaceful, and such a beautiful space. Amazing high ceilings and natural light. The yard is gorgeous, so I can only imagine how lovely it is when the weather is warm. Ashton himself is very responsive and accommodating. I was sad to leave!

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

We had an amazing stay at Alissa and Danny’s house! The location is perfect—convenient to everything we needed, yet peaceful and relaxing. The house is carefully designed with families in mind, especially with kids. It has everything you could possibly need for young children, from toys to safety features, making it so easy to enjoy our time there. We were so impressed that we’ve already booked again for our next trip! Highly recommend for any family looking for a comfortable, family-friendly! Mine Gur

Amazing host and great property! Had an amazing time - thank you Daniel!!

Had a great weekend. We felt right at home and comfortable. Close to town and winery’s.

Beautiful home, gave our family lots of room to spread out and sit and enjoy our company together. Modern new build, exactly the place we wanted.

My family went to Stephanie’s home for a relaxing fall weekend in Montauk. Stephanie was very responsive whenever I messaged or texted her, which I appreciated very much. The house was well appointed and fit our needs perfectly! We enjoyed the home and would definitely look to rent this house again!! Wonderful weekend.

A brief stay but a great stay. It was offseason but we got lucky with sunny October weather. The stay was less than a 5 minute drive from the main village with tons of shops, cafes, etc.. the room itself had a beautiful ocean view and was very clean and comfy. Nice shower, comfy beds, plenty of linens and towels provided. Parking included. Overall a very nice stay.

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!

Lovely stay in greenport! Short drive from major north fork activities. Can imagine its even better during the busy season!

This stay was even nicer than its pictures. Went during “off season”, so many places were closed in the area. However, the actual airbnb made up for that. It was beautiful, peaceful, and quiet. We had our own ocean view and easy beach access.

We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.

Overall relaxing stay and trip to Greenport. Sherri is very communicative and her instructions and listing is clear and accurate. The condo is well decorated and clean and has everything you need for a nice weekend. One thing to note- we were aware check in is between 3 and 5 pm based on the listing (wound up being around 4) but it would be nice for it to be earlier. Still 5 stars though!

We really enjoyed our stay. The unit was just enough space for my husband and I and our two daughters. Having a kitchen to prepare quick breakfasts in the morning before heading out for the day and having the pool and beach in the late afternoons gave us everything we needed to start and end busy days at the Hamptons Classic or visiting family. We are hopeful to visit again!

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!

The appointments were rich and exquisite. By far the nicest of a dozen places we’ve tried. The master bedroom was a suite of bathing, dressing, sitting and sleeping quarters and there were three more bedrooms with private baths. The two basement bedrooms were serviceable and spacious.

We had an amazing time staying at this house! It was in a great location, well-stocked with everything we needed, and the host was incredibly responsive. The check-in process was seamless, making our stay even more enjoyable. My family and I had a wonderful experience, and we would definitely book again!

Ellen’s home was the perfect stay for my group! Amazing location and her home was exactly as described in the listing. Ellen was super responsive throughout our stay, and accommodating with early check in and late check out. The backyard pool is the perfect place to relax, with sun hitting different spots all day long, and a perfect amount of privacy from neighbors. The bathrooms and bedrooms provided the ideal set up with clean towels and comfy beds. 10/10 would come back and can’t recommend enough!

My family had a great stay. Mary Ann was sweet and helpful. Very comfortable home with tons of amenities that we enjoyed. The kids really liked helping to feed the chickens and all the natural wild life at the property. Highly recommend for family or groups.

Beautiful home worked perfect for our wedding visit. Loved sitting on the deck! Beautiful landscaping and very private! We were very confortable and able to relax between events and visit. Donna wad very flexible and allowed us to enter early so a dew of our family members could do s little remote eork. I hope to rent here again in the future! As a special surprise we saw the northern lights from the deck one night!!

One could not ask for a better hosts than Christina and Phil - they are extremely communitive, proactive and helpful. Their house is beautiful - gourmet kitchen, in-ceiling speakers throughout the house, nice deck, pool and a picturesque location. The master bedroom has access to the back deck and a great shower. We had all three bedrooms full and everyone enjoyed their stay. We did not take advantage of the kitchen, but if we come back to the Hamptons we would stay here for longer and cook some meals. We are art collectors, so definitely appreciated the works Christina & Phil have amassed. The one thing I would bring to the attention of future renters is that you definitely know you are in somebody else's home - this is the first time we have unpacked only to find that every drawer was full, so we had to place stuff on top of the dresser or on the few open shelves in the closet. That said - totally worth it and would definitely recommend this Airbnb. Hope to be back soon!

Mike’s place made for the perfect Hamptons vacation. The location was the perfect starting point for day trips to Montauk and the harbors and we enjoyed the short walk to the beach daily… but there really is no need to leave this amazing property. Our family cannot stop raving about the amazing outdoor setup that we took full advantage of every day. Mike was very responsive and provided a detailed guide for the house and excellent recommendations for the area. We would 100% book again when we’re in the area and would recommend this place to anyone looking for an amazing Hamptons experience.