The Roundtree Amagansett Offers An Idyllic Escape Out East

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Turning into the entrance of The Roundtree Amagansett felt like slipping into a quiet corner of the Hamptons I’d never known before. My husband of twenty-four hours and I were excited to spend a few days post-wedding in a part of New York we’ve always loved visiting. After the excruciating Friday-afternoon haul out of the city, grayscale architecture began to give way to warm, painted landscapes. By the time the sun had set, we’d driven through what felt like hours of foliage, and felt an inexplicable conviction that autumn in the Hamptons might just be our best kept secret.

Checking in at The Roundtree Amagansett was the most seamless process I’ve experienced in all my travels. Just a few days before, a hotel I was staying at for my wedding downgraded my room without explanation and sent up a bucket of ice after a few calls and a couple hours later. My husband and I were exhausted, delighted, and immediately charmed, as sparkling waters were handed to us and we were shown to our cottage.

Inside, the simplest of furniture seemed to channel all the calm of being near the beach without any of the kitsch. A curated snack bar sat next to a primed Nespresso machine. The bed, decked in Frette, was transporting even upon its first impression. That’s the magic of The Roundtree—the attention to detail that makes you feel an immediate, and lasting, sense of tranquility; like a second home made up just for you.

The Roundtree’s Origin Story

Founded in 2020, the hotel has mastered flexibility while establishing itself as the newest must-stay spot in Amagansett. Unlike other hotels in the area, the hope isn’t to see and be seen. The private 15-room independently-owned, luxury boutique property is inspired by the area’s historic farmsteading legacy, dating back to the 1700s. The property features 5 cottages (one of them is over 250 years old), and a mix of 10 rooms and suites housed in a 100-year-old barn, plus the main house.

Set Apart

Individuality can sometimes feel overdone in the context of a boutique hotel. At The Roundtree Amagansett, the effect couldn’t have been more opposite. The cottage we called home for a few nights offered comfortable space for both of us, like a clever design that felt incredibly intimate, despite access to the rest of the property just outside our front door.

Each morning, guests are offered complimentary continental breakfast, either in their private rooms or via outdoor dining. Carling menu cards can be ticked off and placed on the door handle for room service. We opted to enjoy our breakfast al fresco with a copy of the paper both mornings. Other guests were quiet and friendly.

On The Grounds

It turns out, breakfast is only the beginning when it comes to the amenities The Roundtree Amagansett offers. Beyond the living quarters, a beautifully manicured field is home to small clusters of seating and hanging swings. An ideal wedding venue, the lawn can transform to the idyllic event dreams are made of. During a regular weekend, outdoor games are left out for guests to enjoy. I opted to read in a large swing chair under clear blue skies one afternoon. Tea is served in the afternoon, but the real star of the show comes after dark. Supplies for s’mores are set out at two separate, controlled bonfires.

We capitalized on the hotel’s fleet of bikes and took the scenic route to our seafood dinner one night. Ice cream happy hour starts at 7pm. Lemon water is on constant tap. Parking passes for the beach are available at the front desk. These details add up to an easy, seamless trip to a part of the state where insider knowledge rules. Leave it to The Roundtree Amagansett to transport you—no matter the season or the celebration.

5 more reasons to love The Roundtree Amagansett:

1. Take your relaxation to the next level with private massages or facials by Cornelia Zicu in the comfort of your own space.
2. Share the bliss of Amagansett with your furry friends. The Roundtree is a dog-friendly property.
3. A lovely curation of local products is offered for purchase, including darling beach bags and branded merchandise.
4. Upon arrival, expect a mini bar stocked with an exceptional assortment of snacks and beverages, all complimentary with your stay.
5. Hop on one of the property’s beach cruisers after picking up anything you might need for a day in the sand, like beach chairs, towels, umbrellas, portable ice coolers and even sand toys–all available to guests.