Holiday rentals with outdoor seating in Wainscott

The house was so cozy and comfortable and well stocked. I didn't even miss not having a tv. there are games, records to play on the record player, and plenty of kitchen utensils and spices to experiment in the kitchen. I enjoyed relaxing by the fireplace and walking in the neighborhood. You will need a car to be able to access restaurants and shopping, but it was a short drive. It was exactly what I was hoping for and would return again.

Great place for a small family. Short walk to town. Quiet and private backyard for hanging out by the pool. Eric and his team were very responsive to all of our needs. We would 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

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.

Beautiful home worth the stay

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!

Had a wonderful stay at Maher’s home for a long weekend. The house was spacious and comfortable and we really liked the location. The backyard has a nice deck and outdoor shower! Maher was extremely responsive and helpful all weekend. Would definitely stay here again!!

Dewey’s place is such a dream! Everything is freshly renovated and just feels so crisp, clean, and stylish. You can tell so much love went into the design it’s the perfect mix of modern and cozy. We felt right at home the second we walked in. The kitchen is gorgeous, the bathrooms are spa-like, and every little detail was just so well thought out. Dewey was the sweetest host super responsive and made everything totally seamless. The location is amazing too quiet and peaceful, but still close to all the fun spots (beach, town, restaurants). We didn’t want to leave! Already planning our next trip back. If you’re thinking about booking, do it you’ll love it just as much as we did!

Claudias place might be my favorite air bnb I have stayed at. She has EVERYTHING you could ever think of! The kitchen is stocked with supplies and coffee, which I really appreciated. It was extremely clean and so cozy and felt like your own little space. It is comfortable, private, and a perfect get away from the city. Great for visiting Hamptons if you have a car! Also love her recommendations. I would come back here again and would recommend it without reserve!

We were a party of 5 women and we had a wonderful stay. The location was great, the unit was spotless and spacious, the kitchen had all the necessities, the towels and linens provided were very nice quality, and Amanda was a wonderful host and very responsive. We were able to check-in early which is always an added bonus. The only thing we would recommend being disclosed is that the train is right behind the location and came through pretty early in the morning and was quite loud. Also worth mentioning in the description would be the amount of stairs to get up to the living area of the home. This was not an issue for us, but could be difficult if you had large suitcases and heavy items to carry up. We would definitely recommend and would stay again.

I love this place. Perfect but what we were looking for. Walking distance to access beach. Overlooking the pier. Very clean and check in with.

This was a very comfortable place to stay. Located conveniently close to the North Ferry. It’s above the local bookshop and has a wonderful balcony overlooking the town. Beds were comfortable, showers got nice and hot with good water pressure and couches were comfortable as well. There is also a great coffee shop right across the street. We loved our stay here and we are looking forward to booking again in the future. Highly recommend.

Amazing place. Sally and Eric were great. Even gave me pointers on where to catch pickleball in the afternoons after a long beach day. 100% recommend.

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!

We loved staying at Melissa’s place. It was small but perfect size for three. It was also so peaceful sitting out in the yard! Super close to the beach and downtown greenport. Would stay again!

The place was spotless and exactly as described. Clean water, plenty of privacy, and a peaceful atmosphere made the stay very relaxing. It was easy to get to the beach by Uber, and Elyse even provided a beach umbrella, chairs, and towels which was a nice touch. Everything was well maintained and easy to navigate. I’ll definitely come back again!

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.

My husband and I had a great stay at Doug’s condo! The unit is in a great location with beautiful views. Parking was super convenient and Doug makes check in a breeze. We enjoyed staying bay side and visited the restaurants nearby which are walking distance! We would definitely return and stay here again.

Place was lovely and beautiful! Place looked like photos and was spotlessly clean! Mia was extremely helpful and responded quickly!

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.

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!