The perfect winter setting for a long weekend away. Walkable to all things Amagansett & easy drives to Montauk & all directional Hamptons. Could not have been more accommodating to myself, wife and our outspoken 4 legged companion. Daily breakfast & s’mores happy hour to top all off

By S. Carrelli: The Round Tree was great! It was a pleasant, quiet, small hotel. Everyone was so nice and the service was great! they had tiny cottages and it was very cozy. The rooms in the cottage were great and they had a fireplace that you could use. They also had s’mores making and a huge lawn with hammocks. I also liked how it was so close to town and you could walk to a lot of places. Another thing I liked was how they had fruit, waters, and cookies in the check-in room. Another convenient thing was they had luggage carts that you could use yourself when you got there. The Round Tree checked all the boxes and I will be going back again!

Leaving this after our fourth (maybe 5th?) stay at The Roundtree. We always have such an amazing time. The hospitality is second to none, the setting is so lovely (garden, rooms, views, etc), breakfast is great whether indoors in winter or outdoors in summer, beautiful beaches just down the way and so calm and relaxing. Our favorite place to stay out East. Truly an oasis and a gem! Thank you team always.

The Roundtree Amagansett is a stunning boutique escape. The grounds are beautiful and peaceful, and the small touches make all the difference — from the complimentary ice cream to the warm, thoughtful service. It feels upscale yet personal, with that “special stay” vibe you don’t find often. Absolutely worth it.

This was the most beautiful property! Every cabin was nicely furnished, the amenities provided was perfect for our family. We loved the nightly bonfires and smores, also we especially Enjoyed the complimentary ice cream service at night. Chef Bawas tasting menu took our breath away with every bite !! Also the service was impeccable. Everyone was so nice and friendly, every one greeted us with a smile. There’s not a single bad thing to say about this property, and would HIGHLY recommend anyone I know to stay here. Thank you all for an amazing experience !!

We'll never stay anywhere else on the island again. We experienced an issue with a booking we had elsewhere as we were en route on a Thursday...at the end of June. Magically there were two spots open here and when I called to confirm that this was actually the case and we were mere minutes from potentially arriving, the woman I spoke with was so kind, gave us a last minute discount, and reached out to the onsite people to let them know we'd be there soon. Every single person working here was amazing (Elena!!) and even better was reachable via text for literally anything you could possibly need. The property is stunning. Not just smoke and mirrors influencer stunning, truly stunning. We originally booked the three bedroom cottage but had some issues with our pup and noise as a few vehicles weren't following drop off rules and they moved us into the Main House essentially ruining us for being able to stay anywhere else on this property. Wow. Anything you needed was in this accommodation-kitchen, DR, LR w/fireplace, 2 BRs, 2.5 baths, and the most amazing front porch to have coffee in the morning or pizza from up the street in the evening. You're right on Main Street so the people watching is top tier. Every morning our selected light breakfast items were delivered and the fridges were restocked daily with free still+ sparking water, an assortment of sodas and a couple creamers. Nespresso pods were replenished each day as was the sweet welcome kit filled with little snacks. The location can't be beat-Amber Waves market and Montauk one direction, downtown Amagansett the other. The stay also comes with a beach pass, which is also amazing. Thank you all so much for the beautiful stay and impeccable service. Top notch.

I had the absolute pleasure of having and hosting my wedding at The Roundtree this September. From the start of our planning the entire team, Annie & Boby were extremely helpful in the entire process. They were easy to reach and gave great recommendations. The grounds itself are beautiful. We couldn't have asked for a better setting. With 14 rooms we were able to accomodate our immediate family which was really special. The rooms were beautiful and the staff fantastic. We hosted our Welcome party, ceremony & reception and brunch on the grounds. It was everything I could have asked for in a location!

We truly loved our stay here! Beyond the magical setting and beautiful rooms, what made it unforgettable was the staff—so welcoming, attentive, and genuinely friendly. Traveling with our dog, we were touched by the thoughtful gesture of providing him with his own bed and bowls, which made us feel right at home. Every detail added to the sense of comfort and care. We will definitely be coming back!

My family and I stayed at the Roundtree during the summer and loved every minute of it. The grounds are beautiful, manicured, and served as an oasis for our Hamptons getaway. The team was world class- made us reservations at otherwise unbookable places, chauffeured us to a beautiful area of the beach, and more. The room was immaculate. Our favorite experience was the charity lemonade stand the team set up for our 5 year old. He has been never happier or more excited!