The Roundtree, Amagansett

Charming, low-key, boutique

273 Main Street, Amagansett 11930


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Indagare Loves

  • The central location in town, within biking distance to the beach
  • The social distancing-friendly accommodations, all of which have private entrances
  • The vast backyard equipped with fire pits, grills, loungers and yard games


Alleviate all concern of Hamptons traffic or beach parking permits when you visit The Roundtree, Amagansett.  Perhaps the biggest draw to the property is its ideal location, mere steps away from Amagansett’s boutique shops and eateries, and an easy bike ride to the beach—beach cruisers readily available to all guests.

With just 15 accommodations making up 18 rooms spread over five cottage buildings, the property is incredibly intimate and private. (Every room has its own separate entrance allowing for an entirely socially distant getaway.)

To walk the grounds is to appreciate the history in which The Roundtree, Amagansett is rooted. The main barn, home to six of the fifteen room options, dates from the 19th century. The grounds pay homage to the area's farming past and exude a quiet peacefulness. Step inside any of the rooms and you will be met with a distinct contrast. Rather than embracing the inherent rusticity of the place, the accommodations themselves are starkly contemporary, and appeal to the modern eye with neutral tones. clean lines and high-tech appliances. If you didn’t know any better, you’d think the buildings were made to look as old as they are just for the aesthetic.

Guests considering a stay here should note the experience is hands-off and self-serve compared to other Hamptons resorts. There is no spa or fitness center, no pool and no restaurant. Breakfast options like yogurt & granola or a pastry plate are served daily, as are afternoon tea, ice cream happy hours, and evening s'mores in the back lawn. But for anything more substantial, you will need to hire a private chef to grill you up a summer BBQ in The Roundtree’s lawn, venture a few hundred feet into town, or head further east to some of Montauk’s bustling restaurants and beach bars.

There's plenty of programming however: guests can join HIIT or low-impact sculpting classes, yoga on the lawn, for example. And those seeking fun in the sun can ride the complimentary electric buggy to the beaches.  Beyond that, a resident “Director of Insiders’ Hampton” has great tips to experience the Hamptons like a local.

Who Should Stay

Anybody looking for a quiet but chic getaway within driving distance of Manhattan will appreciate this property, especially those with furry friends in tow. The Roundtree Amagansett is pet-friendly and a great option for those looking for a low-touch, understated retreat. Families will feel at home in the three-bedroom option, and couples will appreciate the standard rooms.

Written by Bridget McElroy

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